Orthogonal Reactivity in Boryl-Substituted Organotrifluoroborates

被引：76

作者：

Molander, Gary A. ^{[1
]}

Sandrock, Deidre L. ^{[1
]}

机构：

[1] Univ Penn, Roy & Diana Vagelos Labs, Dept Chem, Philadelphia, PA 19104 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 47期

关键词：

D O I：

10.1021/ja807076d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A method was developed for the hydroboration of alkenyl-containing organotrifluoroborates to generate dibora intermediates. The reactivity differences between organotrifluoroborates and trialkylboranes facilitated the cross-coupling of the borane moiety of these intermediates in a highly chemoselective fashion with aryl halides, leaving the trifluoroborate intact for subsequent transformation. A one-pot hydroboration/two-directional cross-coupling sequence was also demonstrated, providing the fully elaborated products in good yields. These conditions were also amenable in the cross-coupling of trialkylboranes to halo-containing organotrifluoroborates. The stability of the trifluoroborate moiety to these conditions allows simple and efficient strategies for complex molecule construction.

引用

页码：15792 / +

页数：3

共 30 条

[1] Platinum-catalyzed tandem diboration/intramolecular allylboration: Diastereoselective access to cyclohexanes bearing 1,3-diols [J].

Ballard, CE ;

Morken, JP .

SYNTHESIS-STUTTGART, 2004, (09) :1321-1324

[2] Synthesis and cross-coupling reactions of tetra alkylammonium organotrifluoroborate salts [J].

Batey, RA ;

Quach, TD .

TETRAHEDRON LETTERS, 2001, 42 (52) :9099-9103

[3] [(E)-GAMMA-(1,3,2-DIOXABORINANYL)ALLYL]DIISOPINOCAMPHEYLBORANE, AN EXCEPTIONAL REAGENT FOR THE STEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF ANTI-1-ALKENE-3,4-DIOLS VIA A MASKED ALPHA-HYDROXYALLYLBORATION [J].

BROWN, HC ;

NARLA, G .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4686-4687

[4] Development, mechanism, and scope of the palladium-catalyzed enantioselective allene diboration [J].

Burks, Heather E. ;

Liu, Shubin ;

Morken, James P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (28) :8766-8773

[5] TRANS-VINYLBORANES FROM 9-BORABICYCLO[3.3.1]NONANE THROUGH DEHYDROBORYLATION [J].

COLBERG, JC ;

RANE, A ;

VAQUER, J ;

SODERQUIST, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) :6065-6071

[6] Cross-coupling reactions of arenediazonium tetrafluoroborates with potassium aryl- or alkenyltrifluoroborates catalyzed by palladium [J].

Darses, S ;

Genet, JP ;

Brayer, JL ;

Demoute, JP .

TETRAHEDRON LETTERS, 1997, 38 (25) :4393-4396

[7] Recent developments in bisdiborane chemistry:: B-C-B, B-C-C-B, B-C=C-B and B-CC-B compounds [J].

Dembitsky, VM ;

Abu Ali, H ;

Srebnik, M .

APPLIED ORGANOMETALLIC CHEMISTRY, 2003, 17 (6-7) :327-345

[8] 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 [J].

Desurmont, G ;

Klein, R ;

Uhlenbrock, S ;

Laloe, E ;

Deloux, L ;

Giolando, CM ;

Kim, YW ;

Pereira, S ;

Srebnik, M .

ORGANOMETALLICS, 1996, 15 (15) :3323-3328

[9] A simple and modular strategy for small molecule synthesis: Iterative Suzuki-Miyaura coupling of B-protected haloboronic acid building blocks [J].

Gillis, Eric P. ;

Burke, Martin D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) :6716-+

[10] Regioselective homologation of bis(boronate) intermediates derived from rhodium-catalyzed diboration of simple alkenes [J].

Kalendra, DM ;

Dueñes, RA ;

Morken, JP .

SYNLETT, 2005, (11) :1749-1751

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