Ethynyl MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis

被引:68
作者
Struble, Justin R. [1 ]
Lee, Sul Joong [1 ]
Burke, Martin D. [1 ]
机构
[1] Univ Illinois, Dept Chem, Howard Hughes Med Inst, Roger Adams Lab, Urbana, IL 61801 USA
基金
美国国家科学基金会;
关键词
MIDA boronates; Iterative cross-coupling; Small molecule synthesis; Alkynes Sonogashira coupling; Diels-Alder; CROSS-COUPLING REACTIONS; ORGANOBORON CHEMISTRY; RADICAL REACTIONS; ESTERS; ACIDS; DERIVATIVES; EFFICIENT; STRATEGY; COMPLEX; SCOPE;
D O I
10.1016/j.tet.2010.04.020
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ethynyl N-methyliminodiacetic acid (MIDA) boronate is a very useful building block for small molecule synthesis. This compound can serve as both a bifunctional acetylene equivalent with the capacity for terminus-selective bis-functionalization and a versatile starting material for the preparation of a wide range of other MIDA boronate building blocks. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4710 / 4718
页数:9
相关论文
共 60 条
[1]  
Abiko A., 2002, ORG SYNTH, V79, P103
[2]   B-PROTECTED HALOBORONIC ACIDS FOR ITERATIVE CROSS-COUPLING [J].
Ballmer, Steven G. ;
Gillis, Eric P. ;
Burke, Martin D. .
ORGANIC SYNTHESES, 2009, 86 :344-+
[3]   A sydnone cycloaddition route to pyrazole boronic esters [J].
Browne, Duncan L. ;
Helm, Matthew D. ;
Plant, Andrew ;
Harrity, Joseph P. A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (45) :8656-8658
[4]   Investigation of the Scope and Regiochemistry of Alkynylboronate Cycloadditions with Sydnones [J].
Browne, Duncan L. ;
Vivat, Jerome F. ;
Plant, Andrew ;
Gomez-Bengoa, Enrique ;
Harrity, Joseph P. A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) :7762-7769
[5]   THE SYNTHESIS OF C-14-LABELLED DIETHYLCARBAMAZINE, 1-DIETHYLCARBAMYL-4-METHYLPIPERAZINE (HETRAZAN) [J].
CHASE, BH ;
DOWNES, AM .
JOURNAL OF THE CHEMICAL SOCIETY, 1953, (DEC) :3874-3877
[6]   AMINES CONTAINING 2-HALOGENOETHYL GROUPS [J].
CHILDS, AF ;
GOLDSWORTHY, LJ ;
HARDING, GF ;
KING, FE ;
NINEHAM, AW ;
NORRIS, WL ;
PLANT, SGP ;
SELTON, B ;
TOMPSETT, ALL .
JOURNAL OF THE CHEMICAL SOCIETY, 1948, (DEC) :2174-2177
[7]  
Coelho A, 2002, SYNLETT, P2062
[8]  
Darses S, 1999, EUR J ORG CHEM, V1999, P1875
[9]   Electronic properties of mononuclear, dinuclear, and polynuclear cobaltacarboranes: Electrochemical and spectroelectrochemical studies [J].
de Biani, FF ;
Corsini, M ;
Zanello, P ;
Yao, HJ ;
Bluhm, ME ;
Grimes, RN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (36) :11360-11369
[10]   A [4+2] cycloaddition strategy to pyridine boronic ester derivatives [J].
Delaney, Patrick M. ;
Huang, Jianhui ;
Macdonald, Simon J. F. ;
Harrity, Joseph P. A. .
ORGANIC LETTERS, 2008, 10 (05) :781-783