Nickel-Catalysis Enabling α-Alkylation of Ketones by Secondary Alcohols

被引:15
作者
Bains, Amreen K. [1 ]
Biswas, Ayanangshu [1 ]
Kundu, Abhishek [1 ]
Adhikari, Debashis [1 ]
机构
[1] Indian Inst Sci Educ & Res IISER Mohali, Dept Chem Sci, Sas Nagar 140306, Punjab, India
关键词
Borrowing hydrogen; Secondary alcohol; Radical reaction; Azo-ligand redox; BORROWING HYDROGEN; DEHYDROGENATION; AUTOTRANSFER;
D O I
10.1002/adsc.202200522
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The alpha-alkylation of ketones utilizing a secondary alcohol has been accomplished by an isolable, bench-stable, inexpensive nickel catalyst affording high yields of beta,beta-disubstituted products. This report contributes a nickel catalyst in the pool of a few scarce examples of base metal discovered for this purpose. The substrate scope can span a wide range including aliphatic, alicyclic, and cyclic secondary alcohols. Functionalization of a cholesterol molecule is also possible following this methodology. The catalyst can interconvert between azo and hydrazo form in a reversible fashion to enable this chemical transformation.
引用
收藏
页码:2815 / 2821
页数:7
相关论文
共 51 条
[11]   Nickel-catalysed chemoselective C-3 alkylation of indoles with alcohols through a borrowing hydrogen method [J].
Bains, Amreen K. ;
Biswas, Ayanangshu ;
Adhikari, Debashis .
CHEMICAL COMMUNICATIONS, 2020, 56 (98) :15442-15445
[12]   Homogeneous Nickel-Catalyzed Sustainable Synthesis of Quinoline and Quinoxaline under Aerobic Conditions [J].
Bains, Amreen K. ;
Singh, Vikramjeet ;
Adhikari, Debashis .
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (23) :14971-14979
[13]   Mechanistic insight into the azo radical-promoted dehydrogenation of heteroarene towards N-heterocycles [J].
Bains, Amreen K. ;
Adhikari, Debashis .
CATALYSIS SCIENCE & TECHNOLOGY, 2020, 10 (18) :6309-6318
[14]   Borrowing Hydrogen-Mediated N-Alkylation Reactions by a Well-Defined Homogeneous Nickel Catalyst [J].
Bains, Amreen K. ;
Kundu, Abhishek ;
Yadav, Sudha ;
Adhikari, Debashis .
ACS CATALYSIS, 2019, 9 (10) :9051-9059
[15]   Iron-Catalyzed α-Alkylation of Ketones with Secondary Alcohols: Access to β-Disubstituted Carbonyl Compounds [J].
Bettoni, Leo ;
Gaillard, Sylvain ;
Renaud, Jean-Luc .
ORGANIC LETTERS, 2020, 22 (05) :2064-2069
[16]   Manganese catalyzed α-methylation of ketones with methanol as a C1 source [J].
Bruneau-Voisine, Antoine ;
Pallova, Lenka ;
Bastin, Stephanie ;
Cesar, Vincent ;
Sortais, Jean-Baptiste .
CHEMICAL COMMUNICATIONS, 2019, 55 (03) :314-317
[17]   Osmium Catalyst for the Borrowing Hydrogen Methodology: α-Alkylation of Arylacetonitriles and Methyl Ketones [J].
Buil, Maria L. ;
Esteruelas, Miguel A. ;
Herrero, Juana ;
Izquierdo, Susana ;
Pastor, Isidro M. ;
Yus, Miguel .
ACS CATALYSIS, 2013, 3 (09) :2072-2075
[18]  
Caine D., 1991, COMPREHENSIVE ORGANI
[19]   α-Alkylation of Ketones with Secondary Alcohols Catalyzed by Well-Defined Cp*CoIII-Complexes [J].
Chakraborty, Priyanka ;
Gangwar, Manoj Kumar ;
Emayavaramban, Balakumar ;
Manoury, Eric ;
Poli, Rinaldo ;
Sundararaju, Basker .
CHEMSUSCHEM, 2019, 12 (15) :3463-3467
[20]   Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis [J].
Corma, Avelino ;
Navas, Javier ;
Sabater, Maria J. .
CHEMICAL REVIEWS, 2018, 118 (04) :1410-1459