Copper(I)‐Catalyzed α‐Acryloyloxylation of Ketones with α, β‐Unsaturated Carboxylic Acids To Form α‐Acryloyloxy Ketones. Issue 3 (24th January 2017)

• Record Type: Journal Article
• Authors: Xu, Jing‐Wen; Ji, Peng‐Yi; Liu, Yu‐Feng; Luo, Wei‐Ping; Liu, Qiang; Guo, Can‐Cheng
• Is Part Of: European journal of organic chemistry. Issue 3(2017)
• Page Start: 734
• Page End: 740
• Publication Date: 2017-01-24
• Subjects: Radical reactions -- Ketones -- Homogeneous catalysis -- Copper -- C‐C coupling; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601346
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An efficient method for the α‐C–H acryloyloxylation of ketones with α, β‐unsaturated carboxylic acids was developed, using copper(I) as a catalyst. The most concise approach to form α‐acryloyloxy ketones is through direct oxidative coupling at the α‐C(sp 3 )–H position of ketones. This method gives the products in high yields, and has a wide substrate scope in terms of both ketones and unsaturated carboxylic acids. A copper(I)‐catalyzed reaction mechanism is proposed based on the results of control experiments. Abstract : An efficient method for the synthesis of α‐acryloyloxy ketones has been developed using copper(I) as a catalyst. The reactions take place under mild conditions, and give satisfactory yields of the target products. The reaction also has a good substrate scope in terms of both ketones and α, β‐unsaturated carboxylic acids.