Formation and synthetic applications of metalated organoboranes

Current Organic Chemistry

Volumn 14, Issue 20, 2010, Pages 2549-2566

  Kliś, Tomasz ^a   Luliński, Sergiusz ^a   Serwatowski, Janusz ^a  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Bimetallic reagents; Cross coupling; Fluoride sensing; Metalation; Organoboranes

Indexed keywords

FLUORINE COMPOUNDS; REAGENTS; SYNTHESIS (CHEMICAL); ZIRCONIUM COMPOUNDS;

ALKENYLBORANE; BIMETALLIC REAGENT; BIMETALLICS; CROSS-COUPLINGS; FLUORIDE SENSING; FUNCTIONALIZED; METALATIONS; ORGANICS; ORGANO-BORANES; SYNTHETIC APPLICATION;

METHYL ESTER;

EID: 78649949950     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527210793358259     Document Type: Article

References (86)

1. Rathke, M.W.; Kow, R. Generation of boron-stabilized carbanions. J. Am. Chem. Soc., 1972, 94, 6854.
2. Glogowski, M.E.; Zumbulyodis, N.; Williams, J.L.R. Boron photochemistry XVI. Base stabilization of dimesitylboryl-containing dyes and related 11B NMR studies. J. Organomet. Chem., 1982, 231, 97.
3. Pelter. A.; Singaram, B.; Williams, L.; Wilson, J. W. The dimesitylboron group in organic synthesis 1. Introduction. Tetrahedron Lett., 1983, 24, 623.
4. Pelter. A.; Singaram, B.; Williams, L.; Wilson, J.W. Hindered organoboron groups in organic chemistry. 18. The production of boron-stabilized carbanions. Tetrahedron, 1993, 49, 2965.
5. Pelter, A.; Williams, L.; Wilson, J.W. The dimesitylboron group in organic synthesis 2. The C-alkylation of alkyldimesitylboranes. Tetrahedron Lett., 1983, 24, 627.
6. Pelter, A.; Warren, L.; Wilson, J.W. Hindered organoboron groups in organic chemistry. 20. Allylations and acylations of dimesitylboron stabilized carbanions. Tetrahedron, 1993, 49, 2988.
7. Wilson, J.W.; Pelter, A.; Garad, M.V.; Pardasani, R. Hindered organoboron groups in organic chemistry. 19. Synthesis of heteroatom substitutes dimesitylborylmethanes. Tetrahedron, 1993, 49, 2979.
8. Pelter, A.; Singaram, B.; Wilson, J.W. The dimesitylboron group in organic synthesis 4. The 'Boron-Wittig' reaction. Tetrahedron Lett., 1983, 24, 635.
9. Pelter, A.; Buss, D.; Pitchford, A. The dimesitylboron group in organic synthesis 7. A unique variant of the Boron-Wittig reaction which stereoselectively yields 1,2-diols. Tetrahedron Lett., 1985, 26, 5093.
10. Pelter, A.; Buss, D.; Cocllough, E.; Singaram, B. Hindered organoboron groups in organic chemistry. 23. The interactions of dimesitylboron- stabilized carbanions with aromatic ketones and aldehydes to give alkenes. Tetrahedron, 1993, 49, 7077.
11. Pelter, A.; Smith, K.; Elgendy, S.M.A.; Rowlands, M. Hindered organoboron groups in organic chemistry. 24. The condensation of aliphatic aldehydes with dimesitylboron-stabilized carbanions to give ketons. Tetrahedron, 1993, 49, 7104.
12. Pelter, A.; Smith, K.; Elgendy, S.M.A. Hindered organoboron groups in organic chemistry. 25. The condensation of aliphatic aldehydes with dimesityl- boryl stabilized carbanions to give alkenes. Tetrahedron, 1993, 49, 7119.
13. Pelter, A.; Vaughan-Williams, G.F.; Rosser, R. M. Hindered organoboron groups in organic chemistry. 21. The reactions of dimesitylboron stabilized carbanions. Tetrahedron, 1993, 49, 3007.
14. Pelter, A.; Singaram, B.; Wilson, J.W. The dimesitylboron group in organic synthesis. 3. Reactions of allyldimesitylborane. Tetrahedron Lett., 1983, 24, 631.
15. Kow, R.; Rathke, M.W. Formation and reactions of boron stabilized carbanions derived from vinylboranes. J. Am. Chem. Soc., 1973, 95, 2715.
16. Matteson, D.S.; Moody, R.J. Deprotonation of 1,1-diboronic esters and reactions of the carbanions with alkyl halides and carbonyl compounds. Organometallics, 1982, 1, 20.
17. Matteson, D.S.; Magumbar, D. Alpha-trimethylsilylboronic esters. Pinacol lithio(trimethylsilyl)methaneboronate homologation of boronic esters with [chloro(trimethylsilyl)phenyl]lithium and comparisons with some phosphorous and sulfur analogs. Organometallics, 1983, 2, 230.
18. Matteson, D.S.; Arne, K.H. Carbanions from deprotonation of α- (phenylthio)alkeneboronic esters. J. Am. Chem. Soc., 1978, 100, 1325.
19. Zweifel, G.; Fisher, R.P.; Hornig, A. A convinient procedure for the synthesis of secondary alcohols from 1-alkynes via the alkylation of boronstabilized carbanions. Synthesis, 1973, 37.
20. Zweifel, G.; Arzoumanian, H. The synthesis fo mixed geminal organometallic compounds. Tetrahedron Lett., 1966, 7, 2535.
21. Binger, P.; Köster, R. Darstellung und Eigenschaften von Cyclopropylboranen. Angew. Chem., 1962, 74, 652.
22. Brown, H.C.; Rhodes, S.P. Synthesis of B-cyclopropyl and Bcyclobutylbicyclo[ 3.3.1]nonane via ring closure of boron intermediates. A convinient entry into cyclopropyl and cyclobutyl derivatives via hydroboration. J. Am. Chem. Soc., 1969, 91, 4306.
23. Cainelli, G.; Dal Bello, G.; Zubiani, G. gem-Dimetallic compounds. On the metal-metal nterconversion between gem-organoboron compounds and nbutyllithium. Tetrahedron Lett., 1965, 6, 3429.
24. Mukaiyama, T.; Murakami, M.; Oriyama, T.; Yamaguchi, M. A new aldol reaction. A method for the generation of vinyloxyboranes by the acylation of boron-stabilized carbanion. Chem. Lett., 1981, 1193.
25. Pelter, A.; Smith, K.; Parry, D.E.; Jones, K.D. The synthesis and some properties of the first boron-stabilized alkenyl carbanions. Aust. J. Chem., 1992, 45, 57.
26. 2-geminated organobismetallic derivatives. Chem. Rev., 2000, 100, 2887.
27. 3-geminated organodimetallics. Chem. Rev., 1996, 96, 3241.
28. Cooke, M.P. Boron-activation of acetylenes to nucleophilic addition reactions. J. Org. Chem., 1994, 59, 2930.
29. Pelter, A.; Smith, K.; Jones, K.D. Allene synthesis via boron-stabilized alkenyl carbanions. J. Chem. Soc., Perkin Trans., 1992, 1, 747.
30. Pelter, A.; Smith, K.; Jones, K. Synthesis and some properties of alkenyl carbanions stabilized by an 􀀁-boron atom. Pure Appl. Chem., 1991, 63, 403.
31. Cooke, M.P.Jr.; Widener, R.K. Nucleophilic addition reactions of hindered unsaturated boranes. New synthesis of organoboranes. J. Am. Chem. Soc., 1987, 109, 931.
32. Cooke, M.P.Jr. Stereochemistry of metal-halogen exchange-initiated intramolecular conjugate addition reactions in the construction of 5-membered carbocycles. J. Org. Chem., 1992, 57, 1495.
33. 2 withα-boralkylmagnesium bromide: a new synthesis of mixed alkyl secondary alcohols. Tetrahedron, 1993, 49, 8877.
34. Braunschweig, H.; D'Andola, G.; Welton, T.; White, A.J.P. Synthesis and structure of novel organocycloborates. Chem. Eur. J., 2006, 12, 600.
35. Braunschweig, H.; D'Andola, G.; Welton, T.; White, A.J.P. Novel organocycloborates via Grignard reagents. Chem. Commun., 2004, 1738.
36. Knochel, P. A new approach to boron-stabilized organometallics. J. Am. Chem. Soc., 1990, 112, 7431.
37. Rozema, M.J.; Siduri, A.R.; Knochel, P. Preparation of functionalized dialkylzinc reagents via an iodine-zinc exchange reaction. Highly enantioselective synthesis of functionalized secondary alcohols. J. Org. Chem., 1992, 57, 1956.
38. Watanabe, T.; Miyaura, N.; Suzuki, A. Stereoselective synthesis of allylic boronates via palladium catalyzed cross coupling reaction of Knochel's (dialkoxyboryl) methylzinc reagents with 1-halo-1-alkenes. J. Organomet. Chem., 1993, 444, C1.
39. Watanabe, T.; Sakai, M.; Miyaura, N.; Suzuki, A. Synthesis of oxo-2- alkenylboronates and their cyclization to 3-methylene cycloalkanols via intramolecular allylboration. J. Chem. Soc. Chem. Commun., 1994, 467.
40. Waas, J. R.; Sidduri, A.; Knochel, P. Preparation and reactions of 1,1-zinc, boron and 1,1-copper, boron alkenyl bismetallics. Tetrahedron Lett., 1992, 33, 3717.
41. Ito, H.; Ito, S.; Sasaki, Y.; Matsuura, K.; Sawamura, M. Copper-catalyzed enantioselective substitution of alkyne carbonates with doboron. An efficient route to optically activeα-chiral allylboronates. J. Am. Chem. Soc., 2007, 129, 14856.
42. Dang, L.; Zhao, H.; Lin, Z.; Marder, T.B. DFT studies of alkene insertions into Cu-B bonds in copper(I) boryl complexes. Organometallics, 2007, 26, 2824.
43. Dang, L.; Lin, Z.; Marder, T.B. DFT studies on the borylation ofα,β- unsaturated carbonyl compounds catalyzed by phosphine copper(I)boryl complexes and observations of the interconversion between O- and C- bound enolates of Cu, B and Si. Organometallics, 2008, 27, 4443.
44. Dang, L.; Zhao, H.; Lin, Z.; Marder, T.B. Understanding the higher reactivity of B2cat2 versus B2pin2 in copper(I) catalyzed alkene diboration reactions. Organometallics, 2008, 27, 1178.
45. Laitar, D.S.; Tsuy, E.Y.; Sadighi, J.P. Copper(I)β-boraldehydes from alkene insertion: isolation and rearrangement. Organometallics, 2006, 25, 2405.
46. Zheng, B.; Srebnik, M. Preparation and selective cleavage reactions of boron- zirconium 1,1-bimetalloalkanes. Tetrahedron Lett., 1993, 34, 4133.
47. Zheng, B.; Srebnik, M. Reactions of N-halosuccinimides with 1,1-bimetallics based on zirconocene and boronic esters: A new synthesis ofα-haloboronic esters. Tetrahedron Lett., 1994, 35, 1145.
48. Skrzypczak-Jankun, E.; Cheesman, B.V.; Lemert, R.M.; Asthana, S.; Srebnik, M. First example of a stable 1,l-bidentate Lewis acid based on boron and zirconium: synthesis, reactivity, X-ray analysis and NMR studies. J. Chem. Soc. Chem. Commun., 1994, 127.
49. Zheng, B.; Deloux, L.; Skrzypczak-Jankun, E.; Cheesman, B.V. Pereira, S.; Srebnik, M.; Sabat, M. A novel class of organometallic complexes: 1,1- bimetallics of boron and zirconium. J. Mol. Struct., 1996, 374, 291.
50. Zheng, B.; Srebnik, M. Synthesis of a new class of bidentate Lewis acids based on boronic esters and zirconocene. J. Organomet. Chem., 1994, 474, 49.
51. Pereira, S.; Srebnik, M. Conjugate addition of gem-borazirconocene alkanes to Michael acceptors. Tetrahedron Lett., 1995, 36, 1805.
52. Zheng, B.; Deloux, L.; Pereira, S.; Skrzypczak-Jankun, E.; Cheesman, B.V.; Sabat, M.; Srebnik, M. Synthesis and reactions of gem-borazirconocenes. Appl. Organomet. Chem., 1996, 10, 267.
53. Zheng, B.; Srebnik, M. Diastereoselective hydrozirconation of optically active 1-alkenyl boryl derivatives: A conversion of 1-alkynes to optically active 1-deuterio primary alcohols. Tetrahedron Lett., 1994, 35, 6247.
54. Zheng, B.; Srebnik, M. Some reactions ofα-allenic boronates. Synth. Commun., 1996, 26, 393.
55. Zheng, B.; Srebnik, M. Use of gem-borazirconocene alkanes in the regioselective synthesis ofα-allenic boronic esters and conversion of the latter to dienes and trienes. J. Org. Chem., 1995, 60, 486.
56. Pereira, S.; Srebnik, M. Facile boron migration during hydrozirconation of alkenylboronates. J. Org. Chem., 1995, 60, 4316.
57. Deloux, L.; Skrzypczak-Jankun, E.; Cheesman, B.V.; Zheng, B.; Sabat, M.; Srebnik, M. First example of stable 1,l-bimetalloalkenes of boron and zirconium: synthesis, reactivity, X-ray analysis, and NMR studies. J. Am. Chem. Soc., 1994, 116, 10302.
58. Deloux, L.; Srebnik, M. Preparation of (Z)-l-alkenyl dioxaborolanes by hydrolysis of boryl zirconocene 1,l-dimetalloalkene. J. Org. Chem., 1994, 59, 6871.
59. Deloux, L.; Srebnik, M. Stereospecific synthesis of Temarotene, its structural isomers, and mixed triaryl alkenes from gem-borazirconocene alkenes. J. Org. Chem., 1995, 60, 3276.
60. Deloux, L.; Srebnik, M. A highly stereocontrolled formal synthesis of rac- Chokols A and G from a common gem-borazirconocene intermediate. Tetrahedron Lett., 1996, 37, 2735.
61. Desurmont, G.; Kein, R.; Uhlenbrock, S.; Laloe, E.; Giolando, D.M.; Kim, Y.W.; Deloux, L.; Pereira, S.; Srebnik, M. Zirconocene-mediated preparation of 1,3-, 1,4-, and 2,3-dibora-1,3-butadienes: their isolation and characterization and use in Suzuki-Miyaura coupling. Organometallics, 1996, 15, 3323.
62. Ben-Valid, S.; Quntar, A.A.; Srebnik, M. Novel vinyl phosphonates and vinyl boronates by halogenation, allylation, and propargylation ofα-boryland_alpha;- hosphonozirconacyclopentenes. J. Org. Chem., 2005, 70, 3554.
63. Quntar, A. A.; Srebnik, M. Preparation of 5-Hydroxy-1-alkenyboronates from 1-alkynylboronates, Cp2ZrCl2/2EtMgBr, and aldehydes. Org. Lett., 2004, 6, 4243.
64. Quntar, A.A.; Botvinik, A.; Rubinstein, A.; Srebnik, M. Synthesis of 3- hydroxy-1-alkenylboronates via phosphine stabilized borylzirconacyclopropenes. Chem. Commun., 2008, 5589.
65. Botvinik, A.; Quntar, A.A.; Rubinstein, A.; Srebnik, M. Synthesis of 2-boryl- 1,3-butadienes from tributylphosphine stabilized zirconacyclopropenes and alkynes. J. Organomet. Chem., 2009, 694, 3349.
66. Metzler, N.; Nöth, H.; Thomann, M. Zirconocene-mediated cyclization of alkynyl-diborylmethanes to 1,3-diborolanes. Organometallics, 1993, 12, 2423.
67. Clark, G.R.; Irvine, G. J.; Roper, W.R.; Wright, L. J. Insertion of ethyne into the Ru-B bond of a coordinatively unsaturated ruthenium boryl complex. X ray crystal structure of Ru(CH=CH[BO2C6H4])Cl(CO)(PPh3)2. Organometallics, 1997, 16, 5499.
68. 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 BPd bond. Organometallics, 2001, 20, 2956.
69. Yamamoto, Y.; Seko, T.; Nemoto, H. New method for the synthesis of boron-10 containing nucleoside derivatives for neutron-capture therapy via palladium-catalyzed reaction. J. Org. Chem., 1989, 54, 4734.
70. Brown, G.R.; Clarke, D.S.; Foubister, A.J.; Freeman, S.; Harrison, P.J.; Johnson, M.C.; Mallion, K.B.; McCormick, J.; McTaggart, F.; Reid, A.C.; Smith, G.J.; Taylor, M.J. Synthesis and activity of a novel series of 3- biarylquinuclidine squalene synthase inhibitors. J. Med. Chem., 1996, 39, 2971.
71. Vedsø, P.; Olesen, P.H.; Hoeg-Jensen, T. Synthesis of sulfonyl chlorides of phenylboronic acids. Synlett, 2004, 892.
72. Dabrowski, M.; Kurach, P.; Luliński, S.; Serwatowski, J. An ortho-lithiated derivative of protected phenylboronic acid: an approach to orthofunctionalized arylboronic acids and 1,3-dihydro-1- hydroxybenzo[c][2,1]oxaboroles. Appl. Organomet. Chem., 2007, 21, 234.
73. Durka, K.; Kurach, P.; Lulíski, S.; Serwatowski, J. Functionalization of dihalophenylboronic acids by deprotonation of their N-butyldiethanolamine esters. Eur. J. Org. Chem., 2009, 4325.
74. White, D.L.; Faller, J. W. Covalently bound paramagnetic shift reagents. 1 A versatile lithium reagent derived from bis[(4-bromophenyl)tris(1- pyrazolyl)borato]cobalt(II). J. Am. Chem. Soc., 1982, 104, 1548.
75. Katz, H.E. New methods for the synthesis of proximally functionalized arylboranes and -silanes. Organometallics, 1986, 5, 2308.
76. Kurach, P.; Lulíski, S.; Serwatowski, J. One-pot generation of lithium (lithiophenyl)trialkoxyborates from substituted dihalobenzenes (Hal = Br, I) and their derivatization with electrophiles. Eur. J. Org. Chem., 2008, 3171.
77. Molander, G.A.; Ellis, N.M. Linchpin synthons: metalation of aryl bromides bearing a potassium trifluoroborate moiety. J. Org. Chem., 2006, 71, 7491.
78. Baron, O.; Knochel, P. Preparation and selective reactions of mixed bimetallic aromatic and heteroaromatic boron-magnesium reagents. Angew. Chem. Int. Ed., 2005, 44, 3133.
79. Caires, C.C.; Guccione, S. Synthesis, structure and reactivity of borate ester coordinated organobismuth compounds. Organometallics, 2008, 27, 747.
80. Melaimi, M.; Gabbaï, F.P. A heteronuclear bidentate Lewis acid as a phosphorescent fluoride sensor. J. Am. Chem. Soc., 2005, 127, 9680.
81. Lee, M. H., Gabbaï, F.P. Synthesis and properties of a cationic bidentate Lewis acid. Inorg. Chem., 2007, 46, 8132.
82. de Rege, F.M.G.; Buchwald, S.L. The regioselective synthesis of halophenols. Tetrahedron, 1995, 51, 4291.
83. de Rege, F.M.G.; Davis, W.M.; Buchwald, S.L. Synthesis and structure of zirconium-group 13 heterobimetallic oompounds. Organometallics, 1995, 14, 4747.
84. Yasuda, S.; Yorimitsu, H.; Oshima, K. Synthesis of aryliron complexes by palladium-catalyzed transmetalation between [CpFe(CO)2I] and aryl Grignard reagents and their chemistry directed toward organic synthesis. Organometallics, 2008, 27, 4025.
85. Retboll, M.; Edwards, A. J.; Rae A. D.; Willis, A. C., Bennett, M. A., Wenger, E. Preparation of benzyne complexes of group 10 metals by intramolecular Suzuki coupling of ortho-metalated phenylboronic esters: molecular structure of the first benzyne-palladium(0) complex. J. Am. Chem. Soc., 2002, 124, 8348.
86. You, Y.; Park, S. Y. A phosphorescent Ir(III) complex for selective fluoride ion sensing with a high signal-to-noise ratio. Adv. Mater., 2008, 20, 3820.