The boron imprint into combined catalytic organic reactions

Current Organic Chemistry

Volumn 15, Issue 23, 2011, Pages 3908-3927

  Bonet, Amadeu ^a   Gulyás, Henrik ^a   Fernández, Elena ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

Bis(catecholato)diboron; Bis(pinacolato)diboron; Boration; Cross coupling; Cyclization; Dimerization

Indexed keywords

CYCLIZATION; REACTION INTERMEDIATES;

BIS(CATECHOLATO)DIBORON; BIS(PINACOLATO)DIBORON; BORATION; CROSS-COUPLINGS; CYCLIZATIONS; DIMERIZATIONS; ORGANIC REACTION; ORGANOBORON; SEQUENTIAL REACTION; TARGET MOLECULE;

MOLECULES;

EID: 81255210942     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211798072421     Document Type: Article

References (91)

1. Brown, H. C. in Hydroboration, Wiley-Interscience: New York, 1962.
2. Brown, H. C. in Boranes in Organic Chemistry, Cornell University Press: Ithaca, 1972.
3. Brown, H. C. In Organic Synthesis via Boranes, Wiley-Interscience: New York, 1975.
4. Pelter, A.; Smith, K.; Brown, H. C. In Borane Reagents, Academic Press: New York, 1988.
5. Cragg, G. M. L. In Organoboranes in Organic Synthesis, Dekker: New York, 1973.
6. Onak, T. In Organoborane Chemistry, Academic Press: New York, 1975.
7. Matteson, D. S., Stereodirected Synthesis with Organoboranes, Springer-Verlag, Berlin, 1995.
8. Miyura, N.; Yamada, K.; Suzuki, A. A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Lett., 1979, 20, 3437.
9. Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev., 1995, 95, 2457.
10. Suzuki, A., Metalcatalyzed Cross-Coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, p. 49.
11. Aliprantis, A. O.; Canary, J. W. observation of catalytic intermediates in the suzuki reaction by electrospray mass spectrometry. J. Am. Chem. Soc., 1994, 116, 6985.
12. Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. Novel and convenient method for the stereo- and regiospecific synthesis of conjugated alkadienes and alkenynes via the palladium-catalyzed cross-coupling reaction of 1-alkenylboranes with bromoalkenes and bromoalkynes. J. Am. Chem. Soc., 1985, 107, 972.
13. Suzuki, A. J. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles. Organomet. Chem., 1999, 576, 147.
14. Kohta, S.; Lahiri, K.; Kashinath, D. Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis. Tetrahedron, 2002, 58, 9633.
15. Ishiyama, T.; Yamamoto, M.; Miyaura, N. A Synthesis of (E)-(1-Organo-1-alkenyl)boronates by the palladium-catalyzed cross-coupling reaction of (e)- 1,2-bis(boryl)-1-alkenes with organic halides: a formal carboboration of alkynes via the diboration-coupling sequence. Chem. Lett., 1996, 1117.
16. Miller, S. P. Morgan, J. B.; Nepveux, F. J., Morken, J. P. Catalytic asymmetric carbohydroxylation of alkenes by a tandem diboration/Suzuki cross-coupling/oxidation reaction. Org. Lett, 2004, 6, 131.
17. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. Synthesis of oxygen heterocycles via a palladium-catalyzed C-O bond-forming reaction J. Am. Chem. Soc., 1996, 118, 10333.
18. Mann, G.; Harwig, J. F. Palladium alkoxides: Potential intermediacy in catalytic amination, reductive elimination of ethers, and catalytic etheration. comments on alcohol elimination from Ir(III). J. Am. Chem. Soc., 1996, 118, 13109.
19. Kuwabe, S.; Torraca, K. E.; Buchwald, S. L. Palladium-catalyzed intramolecular C-O bond formation. J. Am. Chem. Soc., 2001, 123, 12202.
20. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. Platinum(0)-catalyzed diboration of alkynes. J. Am. Chem. Soc., 1993, 115, 11018.
21. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, N.; Miyaura, N.; Suzuki, A. Platinum(0)-Catalyzed diboration of alkynes with Tetrakis(alkoxo)diborons: an efficient and convenient approach to cis-Bis(boryl)alkenes, Organometallics, 1996, 15, 713.
22. Brown, S. D.; Armstrong R. W. Synthesis of tetrasubstituted ethylenes on solid support via resin capture. J. Am. Chem. Soc., 1996, 118, 6331.
23. van den Koedijk, C. D.; Blankestein, M. A.; Thijssen, J. H. Speculation on the mechanism of action of triphenylethylene antioestrogens, Biochem. Pharmacol., 1994, 47, 1927.
24. Backes, B. J.; Ellman, J. A. Carbon-carbon bond-forming methods on solid support. Utilization of Kenner's "Safety-Catch" Linker. J. Am. Chem. Soc., 1994, 116, 11171.
25. Frenette, R.; Friesen, R. W. Biaryl synthesis via suzuki coupling on a solid support. Tetrahedron Lett., 1994, 35, 9177.
26. Boojamra, C. G.; Burow, K. M.; Ellman, J. A. An expedient and highyielding method for the solid-phase synthesis of diverse 1,4-benzodiazepine- 2,5-diones, J. Org. Chem., 1995, 60, 5742.
27. Goff, D. A.; Zuckermann, R. N. Solid-phase synthesis of defined 1,4-benzodiazepine-2,5-dione mixtures J. Org. Chem., 1995, 60, 5744.
28. Lillo, V.; Mas-Marzá, E.; Segarra, A. M.; Carbó, J. J.; Bo, C.; Peris, E.; Fernández, E. Palladium-NHC complexes do catalyze the diboration of alkenes: mechanistic insights. Chem. Commun., 2007, 3380.
29. Pubill-Ulldemolins, C.; Mata, J.; Bo, C.; Fernández, E. Perceptible influence of Pd and Pt-heterocyclic carbene-pyridyl complexes in catalytic diboration of cyclic alkenes. Chem. Asian J., 2010, 5, 261.
30. Lillo, V.; Geier, M. J.; Westcott, S. A.; Fernández, E. Ni and Pd mediate asymmetric organoboron synthesis with ester functionality at the β position. Org. Biomol. Chem. 2009, 7, 4674.
31. Penno, D.; Lillo, V.; Koshevoy, I. O.; Sanaú, M.; Ubeda, M. A.; Lahuerta, P.; Fernández, E. Multifaceted palladium catalysts towards the tandem diboration-arylation reaction of alkenes. Chem. Eur. J. 2008, 14, 10648.
32. Ishiyama, T.; Nishijima, K.; Miyaura, N.; Suzuki, A. Palladium(0)- catalyzed thioboration of terminal alkynes with 9-(alkylthio)-9- borabicyclo[3.3.1]nonane derivatives: stereoselective synthesis of vinyl sulfides via the thioboration-cross-coupling sequence. J. Am. Chem. Soc., 1993, 115, 7219.
33. Cui, Q.; Musaev, D. G. Morokuma, K. Density functional study on the mechanism of Palladium(0)-Catalyzed thioboration reaction of alkynes. Differences between Pd(0) and Pt(0) catalysts and between thioboration and diboration. Organometallics, 1998, 17, 1383.
34. Suginome, M.; Nakamura, H.; Ito, Y. Regio- and stereo-selective silaboration of alkynes catalysed by palladium and platinum complexes. Chem. Commun., 1996, 2777.
35. Suginome, M.; Matsuda, T.; Nakamura, H.; Ito, Y. Regio-and stereoselective synthesis of (Z)-β-silylalkenylboranes by silaboration of alkynes catalyzed by palladium and platinum complexes Tetrahedron, 1999, 55, 8787.
36. Suginome, M.; Ohmori, Y.; Ito, Y. β-Borylallylsilanes as a New Tool for Convenient Synthesis of Alkenylboranes. J. Am. Chem. Soc., 2001, 123, 4601.
37. Suginome, M.; Ohmori, Y.; Ito, Y. Stereoselective construction of trans-1,2- benzooxadecaline frameworks by three-component cascade reactions of an α-phenethyl-β-borylallylsilane with aldehydes. Chem. Commun., 2001, 1090.
38. Suginome, M.; Ohmori, Y.; Ito, Y. Palladium-catalyzed regioselective silaboration of 1,2-dienes. J. Organomet. Chem., 2000, 611, 403.
39. Woodward, A. R.; Burks, H. E; Chan, L. M.; Morken, J. P. Concatenated catalytic asymmetric allene diboration/allylation/functionalization. Org. Lett., 2005, 7, 5505.
40. Sieber, J. D.; Morken, J. P. Sequential Pd-Catalyzed asymmetric allene Diboration/α-Aminoallylation. J. Am. Chem. Soc., 2006, 128, 74.
41. Pelz, N. F.; Morken, J. P. Modular asymmetric synthesis of 1,2-Diols by single-pot allene diboration/hydroboration/cross-coupling. Org. Lett., 2006, 8, 4557.
42. Pasto, D. J.; Chow, J.; Arora, S. K. Transfer reactions involving boron. XIII. Carbon-carbon bond cleavage during the oxidation of vicinal and geminal bis-boronic esters. Tetrahedron Lett., 1967, 723.
43. Matteson, D. S.; Bowie, R. A. Srivastava, G. Synthesis and reactions of some substituted 1-phenylethaneboronic esters. J. Organomet. Chem., 1969, 16, 33.
44. Wiesauer, C.; Weissensteiner, W. Rhodium catalysed enantioselective hydroboration of alkenylboronic esters with catecholborane. Tetrahedron: Asymmetry, 1996, 7, 5.
45. Burks, H. E.; Liu, Sh.; Morken, J. P. Development, mechanism, and scope of the palladium-catalyzed enantioselective allene diboration. J. Am. Chem. Soc., 2007, 129, 8766.
46. Yang, F-Y.; Cheng, Ch-H, Unusual diboration of allenes catalyzed by palladium complexes and organic iodides: a new efficient route to biboronic compounds. J. Am. Chem. Soc. 2001, 123, 761.
47. Onozawa, S.; Tanaka, M. Oxidative addition of the b-cl bond with palladium species and insertion of alkynes and a vinyl ketone into the resulting B-Pd bond. Organometallics, 2001, 20, 2956.
48. 3-Allyl type. J. Am. Chem. Soc., 2001, 123, 1944.
49. Cui, Q.; Musaev, D. G.; Morokuma, K. Why Do Pt(PR3)2 Complexes catalyze the alkyne diboration reaction, but their palladium analogues do not? A density functional study. Organometallics, 1998, 17, 742
50. Cui, Q.; Musaev, D. G.; Morokuma, K. Molecular orbital study of the mechanism of Platinum(0)-Catalyzed alkene and alkyne diboration reactions, Organometallics, 1997, 16, 1355.
51. Sakaki, S.; Kikuno, T. Reaction of BX2-BX2 (X = H or OH) with M(PH3)2 (M = Pd or Pt). A theoretical study of the characteristic features. Inorg. Chem., 1997, 36, 226.
52. Bonet, A.; Gulyás, H.; Koshevoy, I. O.; Estevan, F.; Sanaú, M.; Ubeda, M. A. Fernández, E. Two consecutive catalytic performances, β-boration/arylation of α,β-unsaturated carbonyl compounds, but only one palladium complex as catalytic system. Chem. Eur. J. 2010, 16, 6382.
53. Molander, G. A.; Petrillo, D. E. Suzuki-miyaura cross-coupling of potassium trifluoroboratohomoenolates. Org. Lett. 2008, 10, 1795.
54. Sumida, Y.; Yorimitsu, H.; Oshima, K. Nickel-Catalyzed borylation of aryl cyclopropyl ketones with Bis(pinacolato)diboron to synthesize 4-oxoalkylboronates. J. Org. Chem., 2009, 74, 3196.
55. Gridnev, I. D.; Miyaura, N.; Suzuki, A. Convenient one-pot synthesis of vinylic sulfides from thioalkynes via a catalytic hydroboration-coupling sequence. J. Org. Chem, 1993, 58, 5351.
56. Lee, T.; Baik, Ch.; Jung, I.; Song, K. H.; Kim, S.; Kim, D.; Kang, S. O.; Ko, J. Stereoselective hydroboration of diynes and triyne to give products containing multiple vinylene bridges: A versatile application to fluorescent dyes and light-emitting copolymers. Organometallics, 2004, 23, 4569.
57. Stevens, B. D.; Bungard, Ch. J.; Nelson, S. G. Strategies for expanding structural diversity available from olefin isomerization-claisen rearrangement reactions. J. Org. Chem., 2006, 71, 6397.
58. Lillo, V.; Mata, J. M.; Segarra, A. M.; Peris, E.; Fernández, E. The active role of NHC ligands in platinum-mediated tandem hydroboration-cross coupling reactions. Chem. Commun., 2007, 2184.
59. Tucker, C. E. Knochel, P. Mild and stereoselective hydroborations of functionalized alkynes and alkenes using pinacolborane. J. Org. Chem., 1992, 57, 3482.
60. Wood W. G.; Strong, P.L. 4,4,6-Trimethyl-1,3,2- dioxaborinane. A Stable Dialkoxyborane. J. Am. Chem. Soc., 1966, 88, 4667.
61. Zhang, J.; Lou, B.; Guo, G.; Dai, L. Reversed regiochemistry in the hydroboration of vinylarenes catalyzed by neutral rhodium complexes and the related asymmetric version. J. Org. Chem., 1991, 56, 1670
62. Burgess, K.; Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker R. T.; Calbrese, J. C. Reactions of catecholborane with Wilkinson's catalyst: implications for transition metal-catalyzed hydroborations of alkenes. J. Am. Chem. Soc., 1992, 114, 9350.
63. Bedford R. B.; Hazelwood, S. L.; Albisson, D. A. platinum catalysts for suzuki biaryl coupling reactions. Organometallics, 2002, 21, 2599.
64. Matos, K.; Soderquist, J. A. Alkylboranes in the Suzuki-Miyaura coupling: Stereochemical and mechanistic studies. J. Org. Chem. 1998, 63, 461.
65. Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. Boronic Acids: New coupling partners in room-temperature suzuki reactions of alkyl bromides. crystallographic characterization of an oxidative-addition adduct generated under remarkably mild conditions. J. Am. Chem. Soc. 2002, 124, 13662.
66. Doucet, H. Suzuki-Miyaura cross-coupling reactions of alkylboronic acid derivatives or alkyltrifluoroborates with aryl, alkenyl or alkyl halides and triflates. Eur. J. Org. Chem. 2008, 201, 2013.
67. Rubina, M.; Rubin, M.; Gevorgyan, V. Catalytic enantioselective hydroboration of cyclopropenes, J. Am. Chem. Soc, 2003, 125, 7199.
68. Littke, A. F.; Dai, C. Y.; Fu, G. C. Versatile catalysts for the suzuki crosscoupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions. J. Am. Chem. Soc. 2000, 122, 4020.
69. Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C-C, C-N, and C-O bond-forming cross-couplings. J. Org. Chem. 2002, 67, 5553.
70. Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishikawa, M.; Sato, M.; Suzuki, A. Palladium-catalyzed inter- and intramolecular cross-coupling reactions of B-alkyl-9-borabicyclo[3.3.1]nonane derivatives with 1-halo-1-alkenes or haloarenes. Syntheses of functionalized alkenes, arenes, and cycloalkenes via a hydroboration-coupling sequence. J. Am. Chem. Soc. 1989, 111, 314.
71. Dreher, S. D.; Dormer, P. G.; Sandrock, D. L.; Molander, G. A. Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides. reaction discovery using parallel microscale experimentation. J. Am. Chem. Soc. 2008, 130, 9257
72. Hoogenband, A.; Lange, J. H. M.; Terpstra, J. W.; Koch, M.; Visser, G. M.; Korstanje, T. J.; Jastrzebski, J. T. B. H. Ruphos-mediated Suzuki cross-coupling of secondary alkyl trifluoroborates. Tetrahedron Lett. 2008, 49, 4122.
73. Imao, D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. Cross coupling reactions of chiral secondary organoboronic esters with retention of configuration. J. Am. Chem. Soc. 2009, 131, 5024.
74. Chemler, S. R.; Trauner, D.; Danishefsky, S. J. The B-Alkyl suzuki-miyaura cross-coupling reaction: development, mechanistic study, and applications in natural product synthesis. Angew. Chem. Int. Ed., 2001, 40, 4544.
75. Molander, G. A.; Canturk, B. Organotrifluoroborates and monocoordinated palladium complexes as catalysts-a perfect combination for suzuki-miyaura coupling. Angew. Chem. Int. Ed., 2009, 48, 9240.
76. Suginome, M.; Matsuda, T.; Ito, Y. Nickel-Catalyzed silaborative dimerization of alkynes. Organometallics, 1998, 17, 5233.
77. Onodera, G.; Nishibayashi, Y.; Uemura, S. Ruthenium-Catalyzed reductive coupling reaction of propargylic alcohols via Hydroboration of Allenylidene Intermediates. Organometallics, 2006, 25, 35.
78. I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Transition Metal-Catalyzed Carbocyclizations in Organic Synthesis. Chem. Rev. 1996, 96, 635.
79. Trost, B. M. Palladium-catalyzed cycloisomerizations of enynes and related reactions. Acc. Chem. Res. 1990, 23, 34.
80. Schore, N. E. Transition metal-mediated cycloaddition reactions of alkynes in organic synthesis. Chem. Rev. 1988, 88, 1081.
81. Voldhardt, K. P. C. Cobalt-Mediated [2 + 2 + 2]-Cycloadditions: A Maturing Synthetic Strategy. Angew. Chem. Int. Ed. Engl. 1984, 23, 539.
82. Onozawa, Sh.; Hatanaka, Y.; Tanaka, M. Palladium-catalysed borylsilylation of alkynes and borylsilylative carbocyclization of diynes and an enyne compound Chem. Commun., 1997, 1229.
83. Onozawa, Sh.; Hatanaka, Y.; Choi, N.; Tanaka, M. Palladium-catalyzed borylstannylative carbocyclization of diynes and an enyne compound. Organometallics, 1997, 16, 5389.
84. Molander, G. A.; Pfeiffer, D. Organolanthanide-catalyzed cyclization/boration of 1,5- and 1,6-dienes. Org. Lett., 2001, 3, 361.
85. Kinder, R. E.; Widenhoefer, R. A. Rhodium-catalyzed asymmetric cyclization/hydroboration of 1,6-enynes. Org. Lett., 2006, 8, 1967.
86. Marco-Martínez, J.; López-Carrello, V.; Buñuel, E.; Simancas, R.; Cárdenas, D. J. Pd-catalyzed borylative cyclization of 1,6-enynes. J. Am. Chem. Soc., 2007, 129, 1874.
87. Oh, C. H.; Jung, H. H.; Kim, K. S.; Kim, N. The palladium-catalyzed addition of organoboronic acids to alkynes. Angew. Chem. Int. Ed., 2003, 42, 805.
88. Trost, B. M.; Toste, E. D. Pinkerton, A. B. Non-metathesis rutheniumcatalyzed C-C bond formation. Chem. Rev., 2001, 101, 2067.
89. Marco-Martínez, J.; Buñuel, E.; Muñoz-Rodríguez, R.; Cárdenas, D. J. Pdcatalyzed borylative polycyclization of enediynes to allylboronates. Org. Lett., 2008, 10, 3619.
90. Desurmont, G.; Dalton, S.; Giolando, D. M.; Srebnik, M. Synthesis and selective transformations of 1-alkenyl-4-alkyl diboronates. J. Org. Chem. 1997, 62, 8907.
91. Miura, T.; Murakami, M. Formation of carbocycles through sequential carborhodation triggered by addition of organoborons. Chem Commun., 2007, 217.