Selective Acylation of Aryl- and Heteroarylmagnesium Reagents with Esters in Continuous Flow

被引:21
作者
Heinz, Benjamin
Djukanovic, Dimitrije
Ganiek, Maximilian A.
Martin, Benjamin
Schenke, Berthold
Knochel, Paul
机构
[1] Department of Chemistry, Ludwig-Maximilians-Universität, Butenandtstr. 5-13, Munich
关键词
GRIGNARD-REAGENTS; KETONE SYNTHESIS; ACID-CHLORIDES; TRIFLUOROMETHYL KETONES; CARBOXYLIC-ACIDS; CONVENIENT; CHEMISTRY;
D O I
10.1021/acs.orglett.9b04254
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A selective acylation of readily accessible organomagnesium reagents with commercially available esters proceeds at convenient temperatures and short residence times in continuous flow. Flow conditions allow us to prevent premature collapse of the hemiacetal intermediates despite noncryogenic conditions, thus furnishing ketones in good yields. Throughout, the coordinating ability of the ester and/or Grignard was crucial for the reaction outcome. This was leveraged by the obtention of several bisaryl ketones using 2-hydroxy ester derivatives as substrates.
引用
收藏
页码:493 / 496
页数:4
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