Ritter-type amidation of alkylboron derivatives with nitriles

被引：16

作者：

Cazorla, Clement ^{[1
]}

Metay, Estelle ^{[1
]}

Andrioletti, Bruno ^{[1
]}

Lemaire, Marc ^{[1
]}

机构：

[1] Univ Lyon, UCBL, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 49期

关键词：

Alkylboronic; Ritter amidation; Copper; Oxidative nucleophilic substitution; CATALYZED ASYMMETRIC 1,4-ADDITION; ACIDS; ACETONITRILE; AMIDES;

D O I：

10.1016/j.tetlet.2009.09.132

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and facile synthesis of amides from alkylboron compounds and nitriles promoted by copper acetate and BF3 center dot OEt2 at room temperature is disclosed. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：6855 / 6857

页数：3

共 23 条

[1] FeCl3-catalyzed Ritter reaction. Synthesis of amides [J].

Anxionnat, Bruno ;

Guerinot, Amandine ;

Reymond, Sebastien ;

Cossy, Janine .

TETRAHEDRON LETTERS, 2009, 50 (26) :3470-3473

[2] A well feasible and general route to (organoethynyl)difluoroboranes, RHC≡CBF2, and their perfluorinated analogues, RFC≡CBF2 [J].

Bardin, Vadim V. ;

Adonin, Nicolay Yu. ;

Frohn, Hermann-Josef .

JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (07) :699-702

[3] Synthesis of amides using the Ritter reaction with bismuth triflate catalysis [J].

Callens, Emmanuel ;

Burton, Andrew J. ;

Barrett, Anthony G. M. .

TETRAHEDRON LETTERS, 2006, 47 (49) :8699-8701

[4] Metal-free electrophilic fluorination of alkyl trifluoroborates and boronic acids [J].

Cazorla, Clement ;

Metay, Estelle ;

Andrioletti, Bruno ;

Lemaire, Marc .

TETRAHEDRON LETTERS, 2009, 50 (27) :3936-3938

[5] Regioselective ring opening of amino epoxides with nitriles:: An easy synthesis of (2R,3S)- and (2S,3S)-1,3-diaminoalkan-2-ols with differently protected amine functions [J].

Concellón, JM ;

Suárez, JR ;

del Solar, V .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (18) :7447-7450

[6] Potassium organotrifluoroborates: New perspectives in organic synthesis [J].

Darses, Sylvain ;

Genet, Jean-Pierre .

CHEMICAL REVIEWS, 2008, 108 (01) :288-325

[7] Improved Ritter reaction with CF3-containing oxirane for an access to central units of protease inhibitors [J].

Dos Santos, Mickael ;

Crousse, Benoit ;

Bonnet-Delpon, Daniele .

TETRAHEDRON LETTERS, 2009, 50 (08) :857-859

[8] Suzuki-Miyaura cross-coupling reactions of alkylboronic acid derivatives or alkyltrifluoroborates with aryl, alkenyl or alkyl halides and triflates [J].

Doucet, Henri .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (12) :2013-2030

[9]

Hayashi T, 2001, SYNLETT, P879

[10] Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].

Hayashi, T ;

Yamasaki, K .

CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844

← 1 2 3 →