Manganese-Catalyzed Direct Olefination of Methyl-Substituted Heteroarenes with Primary Alcohols

被引:97
作者
Barman, Milan K. [1 ]
Waiba, Satyadeep [1 ]
Maji, Biplab [1 ]
机构
[1] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741246, India
关键词
dehydrogenative coupling; heteroarenes; manganese; olefination; pincer ligands; ASYMMETRIC TRANSFER HYDROGENATION; C BOND FORMATION; SUSTAINABLE SYNTHESIS; PINCER COMPLEXES; STYRYL DYES; AMINES; DEHYDROGENATION; ALKYLATION; KETONES; IRON;
D O I
10.1002/anie.201804729
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, we present the first catalytic direct olefination of methyl-substituted heteroarenes with primary alcohols through an acceptorless dehydrogenative coupling. The reaction is catalyzed by a complex of the earth-abundant transition metal manganese that is stabilized by a bench-stable NNN pincer ligand derived from 2-hydrazinylpyridine. The reaction is environmentally benign, producing only hydrogen and water as byproducts. A large number of E-disubstituted olefins were selectively obtained with high efficiency.
引用
收藏
页码:9126 / 9130
页数:5
相关论文
共 100 条
[1]   A Stable Manganese Pincer Catalyst for the Selective Dehydrogenation of Methanol [J].
Anderez-Fernandez, Maria ;
Vogt, Lydia K. ;
Fischer, Steffen ;
Zhou, Wei ;
Jiao, Haijun ;
Garbe, Marcel ;
Elangovan, Saravanakumar ;
Junge, Kathrin ;
Junge, Henrik ;
Ludwig, Ralf ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (02) :559-562
[2]  
[Anonymous], 2017, Angew. Chem.
[3]  
[Anonymous], 2018, Angew. Chem., DOI DOI 10.1002/ANGE.201709010
[4]  
[Anonymous], 2017, ANGEW CHEM
[5]  
[Anonymous], 2016, ANGEW CHE
[6]   Catalytic Conversion of Nonfood Woody Biomass Solids to Organic Liquids [J].
Barta, Katalin ;
Ford, Peter C. .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) :1503-1512
[7]   Modularly designed transition metal PNP and PCP pincer complexes based on aminophosphines: Synthesis and catalytic applications [J].
Benito-Garagorri, David ;
Kirchner, Karl .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (02) :201-213
[8]   Catalytic Alkylation of Methyl-N-Heteroaromatics with Alcohols [J].
Blank, Benoit ;
Kempe, Rhett .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (03) :924-+
[9]   EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].
BORDWELL, FG .
ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463
[10]   Transfer Hydrogenation of Carbonyl Derivatives Catalyzed by an Inexpensive Phosphine-Free Manganese Precatalyst [J].
Bruneau-Voisine, Antoine ;
Wang, Ding ;
Dorcet, Vincent ;
Roisnel, Thierry ;
Darcel, Christophe ;
Sortais, Jean-Baptiste .
ORGANIC LETTERS, 2017, 19 (13) :3656-3659