Manganese-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Sulfones: A Tool To Access Highly Substituted Vinyl Sulfones

被引:43
作者
Waiba, Satyadeep [1 ]
Barman, Milan K. [1 ]
Maji, Biplab [1 ]
机构
[1] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741246, India
关键词
BORROWING HYDROGEN; ALPHA-ALKYLATION; ALKENE HYDROGENATION; ARYL SULFIDES; OLEFINATION; AMINES; IRON; COMPLEXES; NITRILES; LIGAND;
D O I
10.1021/acs.joc.8b02911
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of first-row-transition-metal catalysts that can match with the reactivities of the noble metals is considered to be challenging yet very much a desirable goal in homogeneous catalysis. It has become even more fascinating to develop processes where these metals show a unique reactivity and selectivity than their higher congeners. Herein, we report on the catalytic activity of a pincer complex of the abundant earth metal manganese for an unprecedented acceptorless dehydrogenative coupling of alkyl sulfones with alcohols. Thus, highly functionalized vinyl sulfones were obtained in moderate to good yields. Both benzylic and aliphatic alcohols could be utilized, and several functional groups including bromides and iodides are tolerated under the reaction conditions. The reaction is environmentally benign, producing dihydrogen and water as byproducts. Preliminary mechanistic experiments involving kinetic, deuterium-labeling, and NMR experiments were performed.
引用
收藏
页码:973 / 982
页数:10
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