Manganese(I)-Pincer Catalyzed ?-Alkylation of Sulfones by Alcohols

被引：15
|
作者：
Lu, Lijun [1 ]
Luo, Jie [1 ]
Milstein, David [1 ]
机构：
[1] Weizmann Inst Sci, Dept Mol Chem & Mat Sci, IL-76100 Rehovot, Israel
来源：
ACS CATALYSIS | 2023年 / 13卷 / 09期
关键词：
manganese-pincer; -alkylation; sulfone; alcohol; dehydrogenation; hydrogenation; ACCEPTORLESS DEHYDROGENATION; MANGANESE; AMINES; HYDROGENATION; OLEFINATION; METHANOL; KETONES; ESTERS; ARYL; H-2;
D O I：
10.1021/acscatal.3c00369
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Sulfones are building blocks in organic synthesis and pharmaceutical chemistry. Direct alpha-alkylation of sulfones using alcohols with water as the sole byproduct is an efficient and promising method for their structural modifications. However, competitive reactions always exist in this transformation that influences the reaction selectivity. For example, in addition to the desired alpha-alkylation, Julia-type olefination and alpha-alkenylation are frequently observed, especially when benzyl alcohol derivatives were used as alkylation reagents. Herein, we report alpha-alkylation of sulfones using alcohols catalyzed by a pincer complex of earth-abundant manganese. The Mn-PNN-bipyridyl complex exhibited good performance in reaction selectivity. The amount of base also had an important influence on the smooth transformation. Aromatic and aliphatic alcohols are suitable alkylation reagents for sulfones at low metal catalyst loading (0.5 mol %), highlighting the practicality of the developed system.
引用
收藏
页码：5949 / 5954
页数：6
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