Utilization of Potassium Vinyltrifluoroborate in the Development of a 1,2-Dianion Equivalent

被引：35

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：

ORGANIC LETTERS | 2009年 / 11卷 / 11期

关键词：

CROSS-COUPLING REACTION; PALLADIUM; DIBORATION; REACTIVITY; CATALYST;

D O I：

10.1021/ol900822j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Previous studies of orthogonally reactive dibora species led to the discovery of a unique reactivity pattern associated with potassium vinyltrifluoroborate. Upon hydroboration, the vinyltrifluoroborate generates a 1,2-diboraethane, which is distinct from the 1,1-dibora intermediates generated when traditional alkenyldialkylboron species undergo hydroboration. The 1,2-dianion equivalent thus generated can be envisioned as a building block for the linkage of two different electrophiles via palladium-catalyzed Suzuki-Miyaura cross-couplings.

引用

页码：2369 / 2372

页数：4

共 21 条

[1] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF ENOL ACETATES OF ALPHA-BROMO KETONES WITH 1-ALKENYLBORON, ARYLBORON, OR ALKYLBORON COMPOUNDS - A FACILE SYNTHESIS OF KETONES AND THEIR ENOL ACETATES [J].

ABE, S ;

MIYAURA, N ;

SUZUKI, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (10) :2863-2865

[2]

Ali H.A., 2001, ORGANOMETALLICS, V20, P3962

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

Batey, RA ;

Quach, TD .

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

[4] 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

[5] Understanding the higher reactivity of B2cat2 versus B2pin2 in Copper(I)-catalyzed alkene diboration reactions [J].

Dang, Li ;

Zhao, Haitao ;

Lin, Zhenyang ;

Marder, Todd B. .

ORGANOMETALLICS, 2008, 27 (06) :1178-1186

[6] Suzuki-Miyaura Cross-Coupling Reactions of Primary Alkyltrifluoroborates with Aryl Chlorides [J].

Dreher, Spencer D. ;

Lim, Siang-Ee ;

Sandrock, Deidre L. ;

Molander, Gary A. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) :3626-3631

[7]

Eisch JJ, 1998, EUR J INORG CHEM, P761

[8] Pd-catalyzed tandem C-N/C-C coupling of gem-dihalovinyl systems: A modular synthesis of 2-substituted indoles [J].

Fang, YQ ;

Lautens, M .

ORGANIC LETTERS, 2005, 7 (16) :3549-3552

[9] A highly selective tandem cross-coupling of gem-dihaloolefins for a modular, efficient synthesis of highly functionalized indoles [J].

Fang, Yuan-Qing ;

Lautens, Mark .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (02) :538-549

[10] 9-borabicyclo[3.3.2]decanes and the asymmetric hydroboration of 1,1-disubstituted alkenes [J].

Gonzalez, Ana Z. ;

Roman, Jose G. ;

Gonzalez, Eduvigis ;

Martinez, Judith ;

Medina, Jesus R. ;

Matos, Karl ;

Soderquist, John A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9218-+

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