Organocatalytic silyl transfer from silylborane to nitroalkenes for the synthesis of β-silyl nitroalkanes and β-silyl amines

被引：9
作者：
Jiang, Chen-Ran
Zhao, Chun-Liang
Guo, Hui-Fang
He, Wei [1 ]
机构：
[1] Tsinghua Univ, Sch Pharmaceut Sci, Beijing 100084, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 50期
基金：
中国国家自然科学基金;
关键词：
SI-B BOND; NUCLEOPHILIC SILICON; CONJUGATE ADDITIONS; ROOM-TEMPERATURE; TERMINAL ALKYNES; COPPER; ACTIVATION; HYDROSILYLATION; COMPLEXES; ALPHA;
D O I：
10.1039/c6cc03840a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The silylation of a wide array of nitroalkenes is achieved by organocatalysts in yields up to 93%. The reaction is carried out in a toluene/water biphasic solvent under operationally simple conditions. Reduction of the nitro group provides efficient access to functionalized beta-silyl amines.
引用
收藏
页码：7862 / 7865
页数：4
相关论文
共 46 条
[1]   Direct electrophilic silylation of terminal alkynes [J].
Andreev, AA ;
Konshin, VV ;
Komarov, NV ;
Rubin, M ;
Brouwer, C ;
Gevorgyan, V .
ORGANIC LETTERS, 2004, 6 (03) :421-424
[2]   Element-element additions to unsaturated carbon-carbon bonds catalyzed by transition metal complexes [J].
Beletskaya, Irina ;
Moberg, Christina .
CHEMICAL REVIEWS, 2006, 106 (06) :2320-2354
[3]   Copper(II)-Catalyzed Silylation of Activated Alkynes in Water: Diastereodivergent Access to E- or Z-b-Silyl-α, β-Unsaturated Carbonyl and Carboxyl Compounds [J].
Calderone, Joseph A. ;
Santos, Webster L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (16) :4154-4158
[4]   Copper(II)-Catalyzed Silyl Conjugate Addition to α,β-Unsaturated Conjugated Compounds: Bronsted Base-Assisted Activation of Si-B Bond in Water [J].
Calderone, Joseph A. ;
Santos, Webster L. .
ORGANIC LETTERS, 2012, 14 (08) :2090-2093
[5]  
Dieter RK, 2002, MODERN ORGANOCOPPER CHEMISTRY, P79, DOI 10.1002/3527600086.ch3
[6]   Nitrogen ligand complexes of metal chlorides as effective catalysts for the highly regio- and chemoselective silylation of hydroxyl groups with hexamethyldisilazane (HMDS) at room temperature [J].
Firouzabadi, H ;
Sardarian, AR ;
Khayat, Z ;
Karimi, B ;
Tangestaninejad, S .
SYNTHETIC COMMUNICATIONS, 1997, 27 (15) :2709-2719
[7]   Organosilicon Molecules with Medicinal Applications [J].
Franz, Annaliese K. ;
Wilson, Sean O. .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (02) :388-405
[8]   One-pot synthesis of hierarchical porous layered hybrid materials based on aluminosilicate sheets and organic functional pillars [J].
Gaona, Aide ;
Maria Moreno, Jose ;
Velty, Alexandra ;
Diaz, Urbano ;
Corma, Avelino .
JOURNAL OF MATERIALS CHEMISTRY A, 2014, 2 (45) :19360-19375
[9]   Nanogold-Catalyzed cis-Silaboration of Alkynes with Abnormal Regioselectivity [J].
Gryparis, Charis ;
Stratakis, Manolis .
ORGANIC LETTERS, 2014, 16 (05) :1430-1433
[10]  
Hartmann E, 2011, CHIM OGGI, V29, P34
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