Coupling of amides with ketones via C–N/C–H bond cleavage: a mild synthesis of 1,3-diketones

文献情報

出版日 2020-08-11

DOI 10.1039/D0QO00797H

インパクトファクター 5.281

著者

Yuanzhi Xia, Sunwoo Lee

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要旨

A variety of aryl and alkyl-substituted tertiary amides react with ketones in the presence of LiHMDS and a variety of primary and secondary amides in one pot to give the corresponding 1,3-diketone products in good to excellent yields via C–N cleavage of amides and deprotonation of ketones. The reaction was conducted at room temperature under transition-metal-free conditions. N-Tosyl-, N-triflyl-, N-mesyl-, and N-Boc-substituted tertiary amides including N-benzoyl saccharin and N-benzoyl succinimide showed good activity in the reaction. The broad scope, good functional group tolerance of substrates and gram-scale synthesis showed the great importance and potential of this protocol in organic synthesis and industrial manufacture.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Coupling of amides with ketones via C–N/C–H bond cleavage: a mild synthesis of 1,3-diketones

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