Rhodium-catalyzed C-C bond cleavage reactions -an update

Current Organic Chemistry

Volumn 16, Issue 10, 2012, Pages 1170-1214

  Korotvička, Aleš ^a   Nečas, David ^a   Kotora, Martin ^a,b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

C C bond cleavage; Catalysis; Rhodium; Synthesis

Indexed keywords

ACTIVATION ANALYSIS; CHEMICAL ACTIVATION; CHEMICAL BONDS; LIGANDS; RHODIUM COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

BOND CLEAVAGE REACTION; BOND CLEAVAGES; C-C BOND ACTIVATION; C-C BOND CLEAVAGE; C-C BONDS; CLASSICAL CONDITIONS; ORGANIC CHEMISTRY; ORGANIC SYNTHESIS; RHODIUM COMPLEXES; RHODIUM-CATALYZED;

CATALYSIS;

EID: 84861180848     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527212800564213     Document Type: Article

References (211)

1. Modern Rhodium-Catalyzed Reactions; Evans, P. A. Ed.; Wiley-VCH: Weinheim, 2005.
2. Mehta, G.; Muthusamy, S. Tandem cyclization-cycloaddition reactions of rhodium generated carbenoids from α-diazo carbonyl compounds. Tetrahedron,2002, 58, 9477-9504.
3. Fagnou, K.; Lautens, M. Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds. Chem.Rev.,2003, 103, 169-196.
4. Hayashi, T.; Yamasaki, K. Rhodium-catalyzedasymmetric 1,4-addition and Its related asymmetric reactions. Chem. Rev.,2003, 103, 3829-2844.
5. Gois, P. M. P.; Afonso, C. A. M. Stereo-and regiocontrolin the formation of lactams by rhodium-carbenoid C-H insertionof α-diazoacetamides. Eur. J. Org. Chem.,2004, 3773-3788.
6. Carroll, A.-M.; Sullivan, T. P. O.; Guiry, P. J. The development of enantioselective rhodium-catalysed hydroboration of olefins. Adv. Synth. Catal.,2005, 347, 609-631.
7. Katsaros, N.; Anagnostopoulou, A. Rhodium and its compounds aspotential agents in cancer treatment. Oncology/Hematology,2002, 42, 297-308.
8. For reviews on transition metal induced C-C bond cleavage, see: Bishop III, K. C. Transition metal catalyzed rearrangements of small ring organic molecules. Chem. Rev.,1976, 76, 461-486.
9. Sarel, S. Metal-induced rearrangements and insertions into cyclopropyl olefins. Acc. Chem. Res.,1978,11, 204-211.
10. Crabtree, R. H. The organometallic chemistry of alkanes. Chem. Rev.,1985, 85, 245-269.
11. Jennings, P. W.; Johnson, L. L. Metallacyclobutane complexes of the group eight transition metals: synthesis, characterization, and chemistry. Chem. Rev.,1994, 94, 2241-2290.
12. Murakami, M.; Ito, Y. Cleavage of carbon-carbon single bonds by transition metals. Top. Organomet. Chem.,1999, 3, 97-129.
13. Rybtchinski, B.; Milstein, D. Metalinsertion into C-C bonds in solution. Angew. Chem. Int. Ed.,1999, 37, 870-883.
14. Jun, C-H. Transition metal-catalyzed carbon-carbon bond activation. Chem. Soc. Rev.,2004, 33, 610-618.
15. Kondo, T. On inventing catalyticreactions via ruthena-and rhodacyclic intermediates for atom economy. Synlett, 2008, 629-644.
16. Park, Y. J.; Park, J.-W.; Jun, C.-H. Metal-organic cooperative catalysis in C-H and C-C bond activation and its concurrent recovery.Acc. Chem. Res.,2008, 41, 222-234.
17. Miura, T.; Murakami, M.Formation of carbocycles through sequential carborhodation triggered by additionof organoborons. Chem. Commun., 2007, 217-224.
18. Winter, C.; Krause, N.Rhodium-catalyzed enantioselective C-C bond activation. Angew. Chem. Int.Ed., 2009, 48, 2460-2462.
19. Williamson, D. E.; Abraham, A. Site Charge Models for Molecular Electrostatic Potentials of Cycloalkanes and Tetrahedrane. J. Comput. Chem., 1999,20, 579-585.
20. For additional information see: Hudlicky, T.; Reed, J. W. In: ComprehensiveOrganic Synthesis, Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford,1991, Vol 5, pp. 899-970 and references therein.
21. Hudlicky, T.; Reed, J. W. From discovery to application: 50 years of the vinylcyclopropane-cyclopentene rearrangement and its impact on the synthesis of natural products. Angew. Chem. Int. Ed., 2010, 49, 4864-4876.
22. Hogeveen, H.; Volger, H. C. Valence isomerization of quadricyclene tonorbornadiene catalyzed by transition metal complexes. J. Am. Chem. Soc.,1969, 89, 2486-2487.
23. Katz, T. J.; Cerefice, S. A. The Mechanism of a Metal-Catalyzed Cycloaddition Reaction. J. Am. Chem. Soc., 1969, 91, 6519-6521.
24. Periana, R. A.; Bergman, R. G. C-C activation of organic small ring compounds by rearrangement of cycloalkylhydridorhodium complexes to rhodacycloalkanes. Synthesis of metallacyclobutanes, including one with a tertiary M-C bond, by nucleophilic addition to π-allyl complexes. J. Am. Chem. Soc.,1986, 108, 7346-7355.
25. Wick, D. D.; Northcutt, T. O.; Lachicotte, R. J.; Jones, W. D. Carbonhydrogenand carbon-carbon bond activation of cyclopropane by a hydridotris (pyrazolyl)borate rhodium complex. Organometallics, 1998, 17, 4484-4492.
26. Chaplin, A. B.; Weller, A. S. C-C bond activation of a cyclopropylphosphine: isolation and reactivity of a tetrameric rhodacyclobutane. Organometallics,2010, 29, 2332-2342.
27. Matsuda, T.; Tsuboi, T.; Murakami, M. Rhodium-catalyzed carbonylation ofspiropentanes. J. Am. Chem. Soc., 2007, 129, 12596-12597.
28. Walczak, M. A. A.; Wipf, P. Rhodium (I)-catalyzed cycloisomerizations ofbicyclobutanes. J. Am. Chem. Soc., 2008, 130, 6924-6925.
29. Ota, K.; Chatani, N. Rh (II)-catalyzed skeletal reorganization of enynesinvolving selective cleavage of C-C triple bonds. Chem. Commun., 2008,2906-2907.
30. Song, L.; Arif, A. M.; Stang, P. J. Interaction of rhodium (I) with cyclopropenones:decarbonylation and formation of l-rhodacyclopentene-2,5-diones andcationic oxygen σ-bound cyclopropenone complexes. X-ray crystal structureof trans -carbonylbis (triphenylphosphine) (di-tert-butylcyclopropenone) rhodiumtrifluoromethanesulfonate. Organometallics, 1990, 9, 2792-2797.
31. Masarwa, A.; Marek, I. Selectivity in Metal-Catalyzed Carbon-Carbon Bond Cleavage of Alkylidenecyclopropanes.Chem. Eur. J., 2010, 16, 9712-9721.
32. Pellissier, H. Recent developmentsin the reactivity of methylene-and lkylidenecyclopropane derivatives. Tetrahedron,2010, 66, 8341-8375.
33. Osakada, K.; Takimoto, H.; Yamamoto, T. Reaction of 1-aryl-2-methylenecyclopropanes with rhodium (I) complexes leading to ring openingisomerization and π co-ordination of the C=C double bond. J. Chem. Soc.,Dalton Trans., 1999, 853-860.
34. Nishihara, Y.; Yoda, M.; Osakada, K. Hydrido-rhodium (I) and -iridium (I) complex promoted ring-opening isomerizationof unsymmetrically substituted methylenecyclopropanes into 1,3-dienes.Structures of intermediates and reaction pathways. Organometallics, 2001,20, 2124-2126.
35. 2Ph). Organometallics, 2004, 23, 5402-5409.
36. Itazaki, M.; Nishihara, Y.; Takimoto, H.; Yoda, M.; Osakada, K. Ring-openingisomerization of methylenecyclopropanes catalyzed by hydridorhodium (I)complexes. J. Mol. Catal. A, 2005, 241, 65-71.
37. Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Y. K.; Donskaya, N. A.; Tveritinova, E. V.; Yuréva, N. M.; Beletskaya, I. P. Synthesis of mono-, di-,and trisilyl-substituted alkenes via the hydrosilylation of methylenecyclopropanescatalyzed by Rh (I) Complexes. J. Org. Chem., 1997, 62, 6069-6076.
38. Bessmertnykh, A. G.; Grishin, Y. K.; Donskaya, N. A.; Beletskaya, I. P.Hydrosilylation of cyclopropyl-substituted methylenecyclopropanes withtriethylsilane catalyzed by Wilkinson's complex. Russ. J. Org. Chem., 1998,34, 790-798.
39. Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Y. K.; Donskaya, N. A.; Tveritinova, E. V.; Beletskaya, I. P. Convenient preparation method of β-silylated olefins by hydrosilylation of methylenecyclopropanesover Rh (I) complexes. Russ. J. Org. Chem., 1998, 34, 799-808.
40. Simaan, A.; Goldberg, A. F. G.; Rosset, S.; Marek, I. Metal-catalyzed ringopeningof alkylidenecyclopropanes: new access to building bocks with anacyclic quaternary stereogenic center. Chem. Eur. J., 2010, 16, 774-778.
41. Simaan, S.; Marek, I. Hydroformylation reaction of alkylidenecyclopropanederivatives: a new pathway for the formation of acyclic aldehydes containingquaternary stereogenic carbons. J. Am. Chem. Soc., 2010, 132, 4066-4067.
42. Evans, A. P.; Inglesby, P. A. Intermolecular rhodium-catalyzed [3+2+2]carbocyclization of alkenylidenecyclopropanes with activated alkynes: regioanddiastereoselective construction of cis-fused bicycloheptadienes. J. Am.Chem. Soc., 2008, 130, 12838-12839.
43. Aïssa, C.; Fürstner, A. A rhodium-catalyzed C-H activation/cycloisomerization tandem. J. Am. Chem. Soc., 2007, 129, 14836-14837.
44. Chiusoli, G. P.; Costa, M.; Melli, L. Rhodium-catalyzed C-C coupling reactionsinvolving ring opening strained molecules. II. Addition to olefins andaromatic substitution. J. Organomet. Chem., 1988, 358, 495-505.
45. Grigg, R.; Hayes, R.; Sweeney, A. Rhodium (I) catalyzed rearrangement ofcyclo-octatetraene epoxide and bicycle [6.1.0]nonatrienes. J. Chem. Soc.,Chem. Commun., 1971, 1248-1249.
46. Salomon, R. G.; Salomon, M. F.; Kachinski, J. L. C. Rhodium (I) catalysis ofvinylcyclopropane epimerization and ring cleavage rearrangements. J. Am.Chem. Soc., 1977, 99, 1043-1054.
47. Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. Cyclopenteneannulation via intramolecular addition of diazo ketones to 1,3-dienes. Applicationsto the synthesis of cyclopentanoid terpenes. J. Org. Chem., 1980, 45,5020-5027.
48. Gassman, P. G.; Lee, C.-J. Vinylcyclopropane rearrangement of ethyl 6-ethenylbicyclo [3.1.0]hexane-1-acetate. Synth. Commun., 1994, 24, 1457-1463.
49. Hayashi, M.; Ohmatsu, T.; Meng, Y.-P.; Saigo, K. Rhodium (I)-catalyzedregioselective ring-expanding rearrangement of allenylcyclopropanes intomethylenecyclopentenes. Angew. Chem. Int. Ed., 1998, 37, 837-839.
50. Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Y. K.; Donskaya, N. A.; Beletskaya, I. P. C-C bond activation of cyclopropane ring in hydrosilylation catalyzed by Wilkinson komplex. Tetrahedron Lett., 1995, 36, 7901-7904.
51. Intramolecular reaction. (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Transition metal catalyzed [5+2] cycloadditions of vinylcyclopropanes andalkynes: A homolog of the Diels-Alder reaction for the synthesis of sevenmemberedrings. Am. Chem. Soc., 1995, 117, 4720-4721.
52. Wender, P. A.;Husfeld, C. O.; Langkopf, E.; Love, J. L. First studies of the transition metalcatalyzed [5+2] cycloadditions of alkenes and vinylcyclopropanes: scope and stereochemistry. J. Am. Chem. Soc., 1998, 120, 1940-1941.
53. Wender, P.A.; Sperandio, D. A new and selective catalyst for the [5+2] cycloaddition of vinylcyclopropanes and alkynes. J. Org. Chem., 1998, 63, 4164-4165.
54. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. L.; Pleuss, N. The first metal-catalyzed intramolecular [5+2] cycloaddition of vinylcyclopropanes and alkenes: scope, stereochemistry, and asymmetric catalysis. Tetrahedron,1998, 54, 7203-7220.
55. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. L. Transition metal catalyzed [5+2] cycloadditions of allenesand vinylcyclopropanes: first studies of endo-exo selectivity, chemoselectivity,relative stereochemistry, and chirality transfer. J. Am. Chem. Soc.,1999, 121, 5348-5349.
56. Wender, P. A.; Dyckman, A. C.; Husfeld, C. O.; Kadereit, D.; Love, J. L.; Rieck, H. Transition metal catalyzed [5+2] cycloadditionswith substituted cyclopropanes: first studies of regio-andstereoselectivity. J. Am. Chem. Soc., 1999, 121, 10442-10443.
57. Wender, P.A.; Dyckman, A. C. Transition metal catalyzed [5+2] cycloadditions of 2-substituted-1-vinylcyclopropanes: catalyst control and reversal of regioselectivity.Org. Lett., 1999, 1, 2089-2092.
58. Wender, P. A.; Williams, T. J.[(Arene)Rh (cod)]+ complexes as catalysts for [5+2] cycloaddition reactions.Angew. Chem. Int. Ed., 2002, 41, 4550-4553.
59. Wender, P. A.; Rieck, H.; Fuji, M. The transition metal-catalyzed intermolecular [5+2] cycloaddition: the homologous Diels-Alder reaction. J. Am. Chem. Soc., 1998, 120, 10976-10977.
60. Wender, P.A.; Dyckman, A. J.; Husfeld, C. O.; Gamber, G. G.; Scanio, M. J. C. A newand practical five-carbon component for metal-catalyzed [5+2] cycloadditions:preparative scale syntheses of substituted cycloheptenones. Org. Lett.,2000, 2, 1609-1611.
61. Wender, P. A.; Dyckman, A. C.; Barzilay, C. M.; Dyckman, A. J. The first intermolecular transition metal-catalyzed [5+2] cycloadditionswith simple, unactivated, vinylcyclopropanes. J. Am. Chem.Soc., 2001, 123, 179-180.
62. Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. Three-component cycloadditions: the first transition metalcatalyzed [5+2+1] cycloaddition reactions. J. Am. Chem. Soc., 2002, 124,2876-2877.
63. Saito, A.; Ono, T.; Hanzawa, Y. Cationic Rh (I) catalyst in fluorinated alcohol:mild intramolecular cycloaddition reactions of ester-tethered unsaturatedcompounds. J. Org. Chem., 2006, 71, 6437-6443.
64. Yu, Y.-X.; Wender, P. A.; Houk, K. N. On the mechanism of [Rh (CO)2Cl]2-catalyzed intermolecular (5+2) reactions between vinylcyclopropanesand alkynes. J. Am. Chem. Soc., 2004, 126, 9154-9155.
65. Peng, L.; Sirios, L. E.; Cheong, P. H.-Y.; Yu, Y.-X.; Hartung, I. V.; Rieck, H.; Wender, P. A.; Houk, K. N. Electronic and steric control of regioselectivitiesin Rh (I)-catalyzed (5 + 2) cycloadditions: experiment and theory. J. Am.Chem. Soc., 2010, 132, 10127-10135.
66. Inagaki, F.; Sugikubo, K.; Miyashita, Y.; Mukai, C. Rhodium (I)-catalyzed intramolecular [5+2] cycloaddition reactions of alkynes and allenylcyclopro-panes:construction of bicyclo-[5.4.0]undecatrienes and bicyclo[5.5.0]dodecatrienes. Angew. Chem. Int. Ed., 2010, 49, 2206-2210.
67. Wender, P. A.; Gamber, G. G.; Scanio, M. J. C. Serial [5+2]/[4+2] cycloadditions:facile, preparative, multi-component syntheses of polycyclic compoundsfrom simple, readily available starting materials. Angew. Chem. Int.Ed., 2001, 40, 3895-3897.
68. Wegener, H. A.; de Meijere, A.; Wender, P. A. Transition metalcatalyzedintermolecular [5+2] and [5+2+1] cycloadditions of allenes andvinylcyclopropanes. J. Am. Chem. Soc., 2005, 127, 6530-6531.
69. Wang, Y.; Wang, J.; Su, J.; Huang, F.; Jiao, L.; Liang, Y.; Yang, D.; Zhang, S.; Wender, P. A.; Yu, Z.-X. A computationally designed Rh(I)-catalzed twocomponent [5+2+1] cycloaddition of ene-vinylcyclopropanes and CO for thesynthesis of cyclooctenones. J. Am. Chem. Soc., 2007, 129, 10060-10061.
70. Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Pham, S. M.; Zhang, L.Multicomponent cycloadditions: the four-component [5+1+2+1] cycloadditionof vinylcyclopropanes, alkynes, and CO. J. Am. Chem. Soc., 2005, 127,2836-2837.
71. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. L. Rhodium-catalyzed[5+2] cycloadditions of allenes and vinylcyclopropanes: asymmetric total synthesis of (+)-dictamnol. Org. Lett., 1999, 1, 137-139.
72. Wender, P. A.; Zhang, L. Asymmetric total synthesis of (+)-aphanamol I based on the transition metal catalyzed [5 + 2] cycloaddition of allenes andvinylcyclopropanes. Org. Lett., 2000, 2, 2323-2326.
73. Wender, P. A.; Bi, F. C.; Brodney, M. A.; Gosselin, F. J. Asymmetric synthesisof the tricyclic core of NGF-inducing Cyathane diterpenes via a transition-metal-catalyzed [5+2] cycloaddition. Org. Lett., 2001, 3, 2105-2108.
74. Jiao, L.; Yuan, C.; Yu, Z.-X. Tandem Rh(I)-catalyzed [(5+2)+1] cycloaddition/aldol reaction for the construction of linear triquinane skeleton: Totalsyntheses of (±)-hirsutene and (±)-1-desoxyhypnophilin. J. Am. Chem. Soc.,2008, 130, 4421-4430.
75. Jiao, L.; Ye, S.; Yu, Z.-X. Rh(I)-catalyzed intramolecular[3+2] cycloaddition of trans-vinylcyclopropane-enes. J. Am.Chem. Soc., 2008, 130, 7178-7179.
76. Ashfeld, B. L.; Martin, S. F. Enantioselective syntheses of tremulenediol Aand tremulenolide A. Tetrahedron, 2006, 62, 10497-10506.
77. Wender, P. A.; Haustedt, L. O.; Lim, J.; Love, J. A.; Williams, T. J.; Yoon, J.-Y. Asymmetric catalysis of the [5+2] cycloaddition reaction of vinylcyclopropanesand π-systems. J. Am. Chem. Soc., 2006, 128, 6302-6303.
78. Lee, S. I.; Park, S. Y.; Park, J. H.; Choi, S. Y.; Chung, Y. K.; Lee, B. Y. Rhodium N-heterocyclic carbene-catalyzed [4+2] and [5+2] cycloadditionreactions. J. Org. Chem., 2006, 71, 91-96.
79. Wender, P. A.; Pedersen, T. M.; Gamber, G. G.; Scanio, M. J. C. Transitionmetal-catalyzed hetero-[5+2] cycloadditions of cyclopropyl imines and alkynes:dihydroazepines from simple, readily available starting materials. J.Am. Chem. Soc., 2002, 124, 15154-15155.
80. Koga, Y.; Narasaka, K. Rhodium catalyzed transformation of 4-pentenylcyclopropanes to bicyclo[4.3.0]nonenones via cleavage of cyclopropane ring.Chem. Lett., 1999, 705-706.
81. Shibata, T.; Maekawa, S.; Tamura, K. Rhodium-catalyzed intramolecularcycloaddition of cyclopropene-ynes triggered by carbon-carbon bond cleavage.Heterocycles, 2008, 76, 1261-1270.
82. Cassar, L.; Eaton, P. E.; Halpern, J. Catalysis of symmetry-restricted reactionsby transition metal compounds. The valence isomerization of cubane. J.Am. Chem. Soc., 1970, 92, 3515-3518.
83. Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. C-C activation inbiphenylene. Synthesis, structure, and reactivity of (C5Me5)2M2(2,2'-biphenyl) (M = Rh, Co). Organometallics, 1997, 16, 2016-2023.
84. Perthuisot, C.; Jones, W. D. Catalytic hydrogenolysis of an aryl-aryl carboncarbonbond with a rhodium Complex. J. Am. Chem. Soc., 1994, 116, 3647-3648.
85. Chaplin, A. B.; Tonner, R.; Weller, A. S. Isolation of a low-coordinate rhodiumphosphine complex formed by C-C activation of biphenylene. Organometallics,2010, 29, 2710-2714.
86. Iverson, C. N.; Jones, W. D. Rhodium-catalyzed activation and functionalization of the C-C bond of biphenylene. Organometallics, 2001, 20, 5745-5750.
87. Volger, H. C.; Hogeveen, H. Valence isomerozation of hexamethyl-Dewar benzene to hexamethylbenzene catalyzed by rhodium (I)-olefin complexes.Rec. Trav. Chim., 1967, 86, 830-831.
88. Volger, H. C.; Gaasbeck, M. M. P. The rhodium diene complex catalyzed valence isomerization ofhexamethylbicyclo [2.2.0]hexa-2,5-diene into hexamethylbenzene. Rec. Trav.Chim., 1968, 87, 1290-1292.
89. Crépin, D.; Dawick, J.; Aïssa, C. Combined rhodium-catalyzed carbon-hydrogen activation and β-carbon elimination to access eight-memberedrings. Angew. Chem. Int. Ed., 2010, 49, 620-623.
90. Seiser, T.; Cramer, N. Enantioselective metal-catalyzedactivation of strained rings. Org. Biomol. Chem., 2009, 7, 2835-2840.
91. Seiser, T.; Cramer, N. Enantioselective rhodium-catalyzed C-C bond activation. Chimia, 2010, 64, 153-156.
92. Seiser, T.; Cramer, N. Rhodium-catalyzed C-C bond cleavage: constructionof acyclic methyl substituted quaternary stereogenic centers. J. Am. Chem.Soc., 2010, 132, 5340-5341.
93. Seiser, T.; Roth, O. A.; Cramer, N. Enantioselective synthesis of indanols from tert-cyclobutanols using a rhodium-catalyzed C-C/C-H activation sequence.Angew. Chem. Int. Ed., 2009, 48, 6320-6323.
94. Shigeno, M.; Yamamoto, T.; Murakami, M. Stereoselective restructuring of3-arylcyclobutanols into 1-indanols by sequential breaking and formation ofcarbon-carbon bonds. Chem. Eur. J., 2009, 15, 12239-12931.
95. Seiser, T.; Cathomen, G.; Cramer, N. Enantioselective construction of indanones from cyclobutanols using a rhodium-catalyzed C-C/C-H/C-C bondactivation process. Synlett, 2009, 1699-1703.
96. Wender, P. A.; Deschamps, N. M.; Sun, R. RhI-catalyzed C-C bond activation:seven-membered ring synthesis by a [6+1] carbonylative ring-expansionreaction of allenylcyclobutanes. Angew. Chem. Int. Ed., 2006, 45, 3957-3960.
97. Seiser, T.; Cramer, N. Enantioselective C-C activation of allenyl cyclobutanes:access to cyclohexenones with quaternary stereogenic centers. Angew.Chem. Int. Ed., 2008, 47, 9294-9297.
98. Seiser, T.; Cramer, N. Rhodium (I)-catalyzed enantioselective activation of cyclobutanols: formation of cyclohexanederivatives with quaternary stereogenic centers. Chem. Eur. J., 2010,16, 3383-3391.
99. Murakami, M.; Amii, H.; Ito, Y. Selective activation of C-C bonds next to a carbonyl group. Nature, 1994, 370, 540-541.
100. Murakami, M.; Amii, H.; Shigeto, K.; Ito, Y. Breaking of the C-C bond of cyclobutanones by rhodium (I) and its extension to catalytic synthetic reactions. J. Am. Chem. Soc.,1996, 118, 8285-8290.
101. Dauglis, O.; Brookhart, M. Decarbonylation of aryl ketones mediated by bulky cyclopentadienylrhodium bis (ethylene) complexes. Organometallics,2004, 23, 527-534.
102. Murakami, M.; Itahashi, T.; Amii, H.; Takahashi, K.; Ito, Y. New dominosequences involving successive cleavage of carbon-carbon and carbon oxygen bonds: discrete product selection dictated by catalyst ligands. J. Am.Chem. Soc., 1998, 120, 9949-9950.
103. van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P.Ligand bite angle effects in metal-catalyzed C-C bond formation. Chem.Rev., 2000, 100, 2741-2769.
104. Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. Rhodium (I)-catalyzed successivedouble cleavage of carbon-carbon bonds of strained spiro cyclobutanones.J. Am. Chem. Soc., 1997, 119, 9307-9308.
105. Murakami, M.; Tsuruta, T.; Ito, Y. Lactone formation by rhodium catalyzedC-C bond cleavage of cyclobutanone. Angew. Chem. Int. Ed., 2000, 39,2484-2486.
106. Matsuda, T.; Shigeno, M.; Murakami, M. Asymmetric synthesisof 3,4-dihydrocoumarins by rhodium-catalyzed reaction of 3-(2-hydroxyphenyl)cyclobutanones. J. Am. Chem. Soc., 2007, 129, 12086-12087.
107. Murakami, M.; Itahashi, T.; Ito, Y. Catalyzed intramolecular olefin insertioninto a carbon-carbon single bond. J. Am. Chem. Soc., 2002, 124, 13976-13977.
108. Matsuda, T.; Makino, M.; Murakami, M. Rhodium-catalyzed addition/ring-opening reaction of arylboronic acids with cyclobutanones. Org. Lett., 2004,8, 1257-1259.
109. Matsuda, T.; Shigeno, M.; Makino, M.; Murakami, M. Enantioselective C-C bond cleavage creating chiral quaternary carbon centers. Org. Lett., 2006, 10,3379-3381.
110. Matsuda, T.; Makino, M.; Murakami, M. Synthesis of seven-membered-ring ketones by arylative ring expansion of alkyne-substituted cyclobutanones.Angew. Chem. Int. Ed., 2005, 44, 4608-4611.
111. Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. Transition metal-catalyzed [6+2] cycloadditions of 2-vinylcyclobutanones and alkenes: a new reactionfor the synthesis of eight-membered rings. J. Am. Chem. Soc., 2000, 122,7815-7816.
112. Huffman, M. A.; Liebeskind, L. S. Synthesis of metallacyclopentenones by insertion of rhodium into cyclobutenones. Organometallics, 1990, 9,2194-2196.
113. 4-vinylketene complexes with alkynesto form phenols. Organometallics, 1992, 11, 255-266.
114. Kondo, T.; Taguchi, Y.; Kaneko, Y.; Niimi, M.; Mitsudo, T. Ru-and RhcatalyzedC-C bond cleavage of cyclobutenones: reconstructive and selectivesynthesis of 2-pyranones, cyclopentenes, and cyclohexenones. Angew. Chem.Int. Ed., 2004, 43, 5369-5372.
115. Kondo, T.; Niimi, M.; Nomura, M.; Wada, K.; Mitsudo, T. Rhodiumcatalyzedrapid synthesis of substituted phenols from cyclobutenones and alkynesor alkenes via C-C bond cleavage. Tetrahedron Lett., 2007, 48, 2837-2839.
116. Huffman, M. A.; Liebeskind, L. S. Rhodium (I)-catalyzed intramolecularcarbocyclic ring fusion: a new approach to medium-sized-ring ketones. J.Am. Chem. Soc., 1993, 115, 4895-4896.
117. Early examples of chelation-assisted C-C bond cleavage.Suggs, W. J.; Jun, C.-H. Directed cleavage of carbon-carbon bonds by transition metals: The α-bonds of ketones. J. Am. Chem. Soc., 1984, 106, 3504-3506.
118. Suggs, W. J.; Jun, C.-H. Synthesis of a chiral rhodium alkyl via metal insertion intoan unstrained C-C bond and use of the rate of racemization at carbon to obtaina rhodium-carbon bond dissociation energy. J. Am. Chem. Soc., 1986,108, 4679-4681.
119. Jun, C.-H.; Kang, J.-B.; Lim, Y.-G. Ring opening andring closure of vinylcyclopropanes on Rh and application to unstrained C-C bond cleavage. Tetrahedron Lett., 1995, 36, 277-280.
120. 3-allyl rhodium (III) complex. Bull. Korean Chem. Soc., 1997, 18, 824-827.
121. Jun, C.-H.; Moon, C. W.; Lee, D. Y. Chelation-assistedcarbon-hydrogen and carbon-carbon bond activation by transition metal catalysts. Chem Eur. J., 2002, 8, 2423-2428.
122. Jun, C.-H.; Moon, C. W.; Lee, H.; Lee, D.-Y. Chelation-assisted carbon-carbon bond activation by Rh (I)catalysts. J. Mol. Catal. A: Chem., 2002, 189, 145-156.
123. Jun, C.-H.; Lee, J.H. Application of C-H and C-C bond activation in organic synthesis. PureAppl. Chem., 2004, 76, 577-587.
124. Jun, C.-H.; Lee, H. Catalytic carbon-carbon bond activation of unstrained ketone by soluble transition-metal complex. J. Am. Chem. Soc., 1999, 121,880-881.
125. Jun, C.-H.; Lee, H.; Lim, S.-G. The C-C bond activation and skeletal rearrangementof cycloalkanone imine by Rh (I) catalysts. J. Am. Chem. Soc.,2001, 123, 751-752.
126. Jun, C.-H.; Lee, H.; Park, J.B.; Lee, D.-Y. Catalytic activation of C-H and CCbonds of allylamines via olefin isomerization by transition metal complexes.Org. Lett., 1999, 1, 2161-2164.
127. Jun, C.-H.; Chung, K.-Y.; Hong, J.-B. C-H and C-C bond activation ofprimary amines through dehydrogenation and transimination. Org. Lett.,2001, 3, 785-787.
128. Jun, C.-H.; Lee, D.-Y; Kim, Y.-H.; Lee, H. Catalytic carbon-carbon bondactivation of sec-alcohols by a rhodium (I) complex. Organometallics, 2001,20, 2928-2931.
129. Lee, D.-Y.; Kim, I.-J.; Jun, C.-H. Synthesis of cycloalkanones from dienesand allylamines through C-H and C-C bond activation catalyzed by a rhodium (I) complex. Angew. Chem. Int. Ed., 2002, 41, 3031-3033.
130. Lim, S.-G.; Jun, C.-H. C-C double bond cleavage of linear α,β-unsaturatedketones. Bull. Korean Chem. Soc., 2004, 25, 1623-1624.
131. Ahn, J.-A.; Chang, D.-H.; Park, Y. J.; Yon, Y. R.; Loupy, A.; Jun, C.-H.Solvent-free chelation-assisted catalytic C-C bond cleavage of unstrained ketoneby rhodium (I) complexes under microwave irradiation. Adv. Synth. Catal., 2006, 348, 55-58.
132. Jun, C.-H.; Lee, H.; Moon, C. W.; Hong, H.-S. Cleavage of carboncarbontriple bond of alkyne via hydroiminoacylation by Rh (I) catalyst. J.Am. Chem. Soc., 2001, 123, 8600-8601.
133. Lee, D.-Y.; Hong, B.-S.; Cho, E.-G.; Lee, H.; Jun, C.-H. A hydroacylation-triggered carbon-carbon triplebond cleavage in alkynes via retro-Mannich type fragmentation. J. Am.Chem. Soc., 2003, 125, 6372-6373.
134. Fung, H. S.; Li, B. Z.; Chan, K. S. Sterically enhanced, selective C (CO)-C (α) bond cleavage of a ketone by rhodium porphyrin methyl. Organometallics,2010, 29, 4421-4423.
135. Tanaka, K.; Sasaki, K.; Takeishi, K.; Sugishima, K. Transition-metal catalyzed rearrangement of 5-alkynals to γ;-alkynylketones and 1-cyclopentenylketones. Chem. Commun., 2005, 4711-4713.
136. Nečas, D.; Turskč, M.; Kotora, M. Catalytic deallylation of allyl-anddiallylmalonates. J. Am. Chem. Soc., 2004, 126, 10222-10223.
137. Turskč, M.; Nečas, D.; Drabina, P.; Sedlák, M.; Kotora, M. Rhodium-catalyzed deallylationof allylmalonates and related compounds. Organometallics, 2006, 25, 901-907.
138. Nečas, D.; Kotora, M. Ring opening of methylenecycloalkenes via the C-C bond cleavage. Org. Lett., 2008, 10, 5261-5263.
139. Shintani, R.; Takatsu, K.; Hayashi, T. Rhodium-catalyzed kinetic resolutionof tertiary homoallylic alcohols via stereoselective carbon-carbon bondcleavage. Org. Lett., 2008, 10, 1191-1193.
140. Sumida, Y.; Takada, Y.; Hayashi, S.; Hirano, K.; Yorimitsu, H.; Oshima, K. Rhodium-catalyzed allylation of aldehydes with homoallylic alcohols by retroallylation and isomerization to saturated ketones with conventional or microwaveheating. Chem. Asian J., 2008, 3, 119-125.
141. For review on retroallylation, see: Yorimitsu, H.; Oshima, K. Metal-mediatedretro-allylation of homoallyl alcohols for highly selective organic synthesis.Bull. Chem. Soc. Jpn., 2009, 82, 778-792.
142. Murakami, K.; Ohmiya, H.; Yorimitsu, H.; Oshima, K. Generation of rhodiumenolates via retro-aldol reaction and its application to regioselective aldolreaction. Tetrahedron Lett., 2008, 49, 2388-2390.
143. Nishimura, T.; Katoh, T.; Takatsu, K.; Shintani, R.; Hayashi, T. Rhodiumcatalyzedasymmetric rearrangement of alkynyl alkenyl carbinols: synthetic equivalent to asymmetric conjugate alkynylation of enones. J. Am. Chem.Soc., 2007, 129, 14158-14159.
144. Shintani, R.; Takatsu, K.; Katoh, T.; Nishimura, T.; Hayashi, T. Rhodiumcatalyzedrearrangement of aryl Bis (alkynyl) carbinols to 3-alkynyl-1-indanones. Angew. Chem. Int Ed., 2008, 47, 1447-1449.
145. Uto, T.; Shimizu, M.; Ueura, K.; Tsurugi, H.; Satoh, T.; Miura, M. Rhodiumcatalyzedoxidative coupling of triarylmethanols with internal alkynes via successive C-H and C-C Bond cleavages. J. Org. Chem., 2008, 73, 298-300.
146. For mechanistic studies involving β-aryl elimination in Rh-complexes, see: Zhao, P.; Hartwing, J. F. Insertions of ketones and nitriles into organorhodium (I) complexes and β-hydrocarbyl eliminations from rhodium (I) alkoxoand iminyl complexes. Organometallics, 2008, 27, 4749-4757.
147. Xue, L.; Ng, K. C.; Lin, Z. Theoretical studies on β-aryl elimination from Rh (I) complexes. Dalton Trans., 2009, 5841-5850.
148. Liou, S.-Y.; van der Boom, M. E.; Milstein, D. Catalytic selective cleavageof a strong C-C single bond by rhodium in solution. Chem. Commun.,1998, 687-688.
149. Rybtchinsky, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. A room temperature direct metal insertion into a nonstrained carboncarbonbond in solution. C-C vs C-H bond activation. J. Am. Chem. Soc.,1996, 118, 12406-12415.
150. Salem, H.; Ben-David, Y.; Shimon, L. J. W.; Milstein, D. Exclusive C-C activation and an apparent α-H elimination with a rhodium phosphinite pincer complex. Organometallics, 2006, 25, 2292-2300.
151. Baksi, S.; Acharyya, R.; Basuli, F.; Peng, S.-M.; Lee, G.-H. Nethaji, M.; Bhattacharya, S. Rhodium-mediated C-C bond activation of 2'-(2',6'-dialkylazo)-4-methylphenols. Elimination and migration of alkyl groups. Organometallics,2007, 26, 6596-6603.
152. Tobisu, M.; Kita, Y.; Chatani, N. Rh (I)-catalyzed silylation of aryl and alkenyl cyanides involving the cleavage of C-C and Si-Si bonds. J. Am.Chem. Soc., 2006, 128, 8152-8153.
153. Tobisu, M.; Kita, Y.; Chatani, N. Rhodium-catalyzed silylation and intramolecular arylation of nitriles via thesilicon-assisted cleavage of carbon-cyano bonds. J. Am. Chem. Soc., 2008,130, 15982-15989.
154. Kita, Y.; Tobisu, M.; Chatani, N. Rhodium-catalyzed alkenylation of nitriles via silicon-assisted C-CN bond cleavage. Org. Let., 2010, 12, 1864-1867.
155. Tobisu, M.; Nakamura, R.; Kita, Y.; Chatani, N. Rhodium-catalyzed reductivecleavage of carbon-cyano bonds with hydrosilane: a catalytic protocolfor removal of cyano groups. J. Am. Chem. Soc., 2009, 131, 3174-3175.
156. Dreis, A. M.; Douglas, C. J. Catalytic carbon-carbon σ bond activation: an intramolecular carbo-acylation reaction with acylquinolines. J. Am. Chem.Soc., 2009, 131, 412-413.
157. Wentzel, M. T.; Reddy, V. J.; Hyster, T. K.; Douglas, C. J. Chemoselectivity in catalytic C-C and C-H activation controlling intermolecular carbocyclizationand hydroarylation of alkenes. Angew. Chem. Int. Ed., 2009, 48, 6121-6123.
158. Tsuji, J.; Ohno, K. Organic syntheses by means of noble metal compounds.XXI. Decarbonylation of aldehydes using rhodium complex. TetrahedronLett., 1965, 3969-3971.
159. Tsuji, J.; Ohno, K. Organic syntheses by means of noble metal compounds. XXXIV. Carbonylation and decarbonylationreactions catalyzed by palladium. J. Am. Chem. Soc., 1968, 90, 94-98.
160. Ohno, K.; Tsuji, J. Organic syntheses by means of noble metal compounds.XXXV. Novel decarbonylation reactions of aldehydes and acyl halidesusing rhodium complexes. J. Am. Chem. Soc., 1968, 90, 99-107.
161. Tsuji, J.; Ohno, K. Decarbonylation reactions using transition metals compounds.Synthesis, 1969, 157-169.
162. Osborn, J. A.; Jardine, F. H.; Young, J.F.; Wilkinson, G. The preparation and properties oftris (triphenylphosphine)halogenorhodium (I) and some reactions thereof includingcatalytic homogenneous hydrogenation of olefins and their derivatives.J. Chem. Soc. A, 1966, 1711-1732.
163. Baird, M. C.; Nyman, C. J.; Wilkinson, G. The decarbonylation of aldehydes by tris(triphenylphosphine)chlororhodium(I). J. Chem. Soc. A, 1968, 348-351.
164. Schrock, R. R.; Osborn, J. A. Preparation and Properties of Some CationicComplexes of Rhodium (I) and Rhodium (III). J. Am. Chem. Soc., 1971,93, 2397-2407.
165. James, B. R.; Young, C. G. Catalytic decarbonylation,hydroacylation, and resolution of racemic pent-4-enals using chiral bis(ditertiary-phosphine) complexes of rhodium. J. Organomet. Chem., 1985, 285,321-332.
166. Kampmeier, J. A.; Harris, S. H.; Wedegaertner, D. K. Tests for free-radicalintermediates in the decarbonylation of aldehydes bytris(triphenylphosphine) chlororhodium (I). J. Org. Chem., 1980, 45, 315-318.
167. Kampmeier, J. A.; Harris, S. H.; Mergelsberg, I. Intramolecular trapping of alkyl-and arylrhodium hydride intermediates in the decarbonylation of aldehydesby chlorotris(triphenylphosphine)rhodium. J. Org. Chem., 1984, 49,621-625.
168. Catalytic decarbonylations: (a) Doughty, D. H.; Pignolet, L. H. Catalyticdecarbonylation of aldehydes. J. Am. Chem. Soc., 1978, 100, 7083.
169. Domazetis, G.; James, B. R.; Tarpey, B.; Dolphin, D. Catalytic activation ofcarbon monoxide. ACS Symp. Ser., 1981, 152, 243-252.
170. Doughty, D. H.; Anderson, M. P.; Casalnuovo, A. L.; McGuiggan, M. F.; Tso, C. C.; Wang, H. H.; Pignolet, L. H. The effect of chelating diphosphine ligands on homogeneous catalytic decarbonylation reactions using cationic rhodium catalysts.Adv. Chem. Ser., 1982, 196, 65-83.
171. Meier, M. D.; Kruse, L. I. Ergolinesynthons: synthesis of 3,4-Dihydro-6-methoxybenz [cd]indol-5 (lH)-one (6-methoxy-Uhle's ketone) and 3,4-Dihydrobenz [cd]indol-5 (1H)-one (Uhle'sketone) via a novel decarboxylation of indole-2-carboxylates. J. Org. Chem.,1984, 49, 3195-3199.
172. Abu-Hasanyan, F.; Goldman, M. E.; Goldman, A.S. Development and mechanistic study of a new aldehyde decarbonylationcatalyst. J. Am. Chem. Soc., 1992, 114, 2520-2536.
173. Beck C. M.; Rathmill, S. E.; Park, Y. J.; Chen, J.; Crabtree, R. H.; Liable-Sands, L. M.; Rheingold, A. L. Aldehyde decarbonylation catalysis under mild conditions. Organometallics,1999, 18, 5311-5317.
174. Kreis, M.; Palmelund, A.; Bunch, L.; Madsen, R. A general and convenient method for the rhodium-catalyzeddecarbonylation of aldehydes. Adv. Synth. Catal., 2006, 348, 2148-2154.
175. For theoretical calculation regarding the reaction mechanism of decarbonylation,see: Fristrup, P.; Kreis, M.; Palmelund, A.; Norrby, P.-O.; Madsen, R. The mechanism for the rhodium-catalyzed decarbonylation of aldehydes: Acombined experimental and theoretical study. J. Am. Chem. Soc., 2008, 130,5206-5215.
176. O'Connor, J. M.; Ma, J. Metal-catalyzed decarbonylation of primary aldehydesat room temperature. J. Org. Chem., 1992, 57, 5075-5077.
177. Taarning, E.; Marsden, R. Unsaturated aldehydes as alkene equivalents in the Diels-Alder reaction. Chem. Eur. J., 2008, 14, 5638-5644.
178. Morandi, B.; Carreira, E. M. Catalytic decarbonylation of epoxyaldehydes: Applications to the preparation of terminal epoxides. Synlett, 2009, 2076-2078.
179. Monrad, R. N.; Marsden, R. Rhodium-catalyzed decarbonylation of aldoses. J. Org. Chem., 2007, 72, 9782-9785.
180. Takahashi, T.; Naito, Y.; Tsuji, J. A simple synthesis of de-AB-cholesta-8 (14),22-dien-9-one by highly stereoselective double Michael addition involvingalkenylcopper-phosphine complex, vinyl ketone, and 2-methyl-2-cyclopentenone followed by Claisen rearrangement and rhodium-promoteddecarbonylation. J. Am. Chem. Soc., 1981, 103, 5261-5263.
181. Hansson, T.; Wickberg, B. A short enantiospecific route to isodaucane sesquiterpenesfrom limonene. On the absolute configuration of (+)-aphanamol Iand II. J. Org. Chem., 1992, 57, 5370-5376.
182. Suri, S. C. A formal total synthesis of modhephene. Tetrahedron Lett., 1993,34, 8321-8324.
183. Zhang, H.; Padwa, A. Application of a stereospecific RhCl(PPh3)3 decarbonylationreaction for the total synthesis of 7-(±)-deoxypancratistatin. TetrahedronLett., 2006, 47, 3905-3908.
184. Collins, J.; Rinner, U.; Moser, M.; Hudlicky, T.; Ghiviriga, I.; Romero, A.E.; Kornienko, A. Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesisof 7-deoxypancratistatin and trans-dihydrolycoricidine. J. Org. Chem.,2010, 75, 3069-3084.
185. Bröhmer, M. C.; Volz, N.; Bräse, S. Thieme chemistry journal awardees -Where are they now? Microwave-assisted rhodium-catalyzed decarbonylationof functionalized 3-formyl-2H-chromenes: a sequence for functionalized chromenes like deoxycordiachromene. Synlett, 2009, 1383-1386.
186. Morgan, B. J.; Mulrooney, C. A.; Kozlowski, M. C. Perylenequinone NaturalProducts: Evolution of the Total Synthesis of Cercosporin. J. Org. Chem.,2010, 75, 44-56.
187. Iley, D. E.; Fraser-Reid, B. A new synthesis of sucrose which demonstratesa novel approach to the synthesis of α-linked disaccharides. J. Am.Chem. Soc., 1975, 97, 2563-2565.
188. Ward, D. J.; Szarek, W. A.; Jones, J.K. N. Decarbonylation of aldehydo sugar derivatives with chlorotris(methyldiphenylphosphine)rhodium (I). Chem. Ind. (London), 1976, 162-163.
189. MacCoss, M.; Chen, A.; Tolman, R. L. Synthesis of all four possiblediastereoisomers of the acyclonucleoside 9- (1,3,4-trihydroxy-2-butoxymethyl)guanidine from carbohydrate precursors. Tetrahedron Lett.,1985, 26, 4287-4290.
190. Andrews, M. A.; Gould, G. L.; Klaeren, S. A. Decarbonylation of unpro-tectedaldose sugars by chlorotris (triphenylphosphine)rhodium (I). A new descentof series approach to alditols, deoxyalditols, and glycosylalditols. J.Org. Chem., 1989, 54, 5257-5264.
191. Wilson, R. M.; Thalji, R. K.; Bergman, R. G.; Ellman, J. A. Enantioselective synthesis of a PKC inhibitor via catalytic C-H bond activation. Org. Lett.,2006, 8, 1745-1747.
192. For reviews see: (a) Ajamian, A.; Gleason, J. L. Two birds with one metallic stone: single-pot catalysis of fundamentally different transformations.Angew. Chem. Int. Ed., 2004, 43, 3754-3760.
193. Morimoto, T.; Kakikuchi, K. Evolution of carbonylation catalysis: no need for carbon monoxide. Angew. Chem. Int. Ed., 2004, 43, 5580-588.
194. Morimoto, T.; Fuji, K.; Tsutsumi, K.; Kakikuchi, K. CO-transfer carbonylation reactions. A catalytic Pauson-Khand-type reaction of enynes withaldehydes as a source of carbon monoxide. J. Am. Chem. Soc., 2002, 124,3806-3807.
195. Shibata, T.; Toshida, N.; Takagi, K. Rhodium complexcatalyzed Pauson-Khand-type reaction with aldehydes as a CO source. J.Org. Chem., 2002, 67, 7446-7450.
196. Shibata, T.; Toshida, N.; Takagi, K.Catalytic Pauson-Khand-type reaction using aldehydes as a CO source. Org.Lett., 2002, 4, 1619-1621.
197. Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakikuchi, K. Aqueous catalytic Pauson-Khand-type reactions of enynes with formaldehyde:Transfer carbonylation involving an aqueous decarbonylationand a micellar carbonylation. Angew. Chem. Int. Ed., 2003, 42, 2409-2411.
198. Yeh, M.-C.; Tsao, W.-C.; Ho, J.-S.; Tai, C.-C.; Chiou, D.-Y.; Tu, L.-H. Rhodium (I)-catalyzed intramolecular cyclohexadienyl Pauson-Khand reaction:facile approach to tricarbocycles. Organometallics, 2004, 23, 792-799.
199. Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakikuchi, K. Catalytic asymmetric Pauson-Khand-type reactions of enynes with formaldehyde in aqueous media. Tetrahedron Lett., 2004, 45, 9163-9166.
200. Kwong, F. Y.; Lee, H.W.; Qiu, L.; Lam, W. H.; Li, Y-M.; Kwong, H. L.; Chan, A. S. C. RhodiumbisbenzodioxanPhoscomplex-catalyzed homogeneous enantioselective Pauson-Khand-type cyclization in alcoholic solvents. Adv. Synth. Catal., 2005,347, 1750-1754.
201. Kwong, F. Y.; Li, Y-M.; Lam, W. H.; Qiu, L.; Lee, H.W.; Yeung, C. H.; Chan, K. S.; Chan, A. S. C. Rhodium-catalyzed asymmetric aqueous Pauson-Khand-type reaction. Chem. Eur. J., 2005, 11, 3872-3880.
202. Yang, L.; Guo, X.; Li, C.-J. The First Decarbonylative Coupling of Aldehydesand Norbornenes Catalyzed by Rhodium. Adv. Synth. Catal., 2010,352, 2899-2904.
203. Yang, L.; Correia, C. A.; Guo, X.; Li, C.-J. A novel catalytic decarbonylativeHeck-type reaction and conjugate addition of aldehydes to unsaturated carbonylcompounds. Tetrahedron Lett., 2010, 51, 5486-5489.
204. Sun, Z.-M-; Zhao, P. Rhodium-mediated decarboxylative conjugate addition of fluorinated benzoic acids: stoichiometric and catalytic transformations. Angew. Chem. Int. Ed., 2009, 48, 6726-6730.
205. Shuai, Q.; Yang, L.; Guo, X.; Baslé, O.; Li, C.-J. Rhodium-Catalyzed Oxidative C-H Arylation of 2-Arylpyridine Derivatives via Decarbonylation of Aromatic Aldehydes. J. Am. Chem. Soc., 2010, 132, 12212-12213.
206. Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. Rhodium-catalyzed reaction of aroyl chlorides with alkynes. J. Org. Chem., 1996, 61, 6941-6946.
207. Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. Rhodium-catalyzed reaction of aroyl chlorides with alkynes or alkenes in the presence of disilanes.J. Organomet. Chem., 1998, 560, 217-222.
208. Sugihara, T.; Satoh, T.; Miura, M.; Nomura, M. Rhodium-catalyzed Mizoroki-Heck-type arylation of alkenes with aroyl chlorides under phosphaneandbase-free conditions Angew. Chem. Int. Ed., 2003, 42, 4672-4674.
209. Gooßen, L. J.; Paetzold, L. New Synthesis of Biaryls via Rh-catalyzed decarbonylativeSuzuki-coupling of carboxylic anhydrides with arylboroxines.Adv. Synth. Catal., 2004, 346, 1665-1668.
210. The price of rhodium as of 7. 10. 2011 was 1600 $/oz. (Source:http://www.platinum.matthey.com/).
211. Toyir, J.; Leconte, M.; Niccolai, G. P.; Candy, J.-P-; Basset, J.-M. Uniqueselectivity for the dimerization of propene on RhSn/SiO2 catalysts: implicationson the mechanism of C-C bond forrnation and cleavage on bimetalliccatalysts. J. Mol. Catal. A, 1995, 100, 61-73.