Rhodium-catalyzed sequential intermolecular hydroacylation and deconjugative isomerization toward diversified diketones

Literature Information

Publication Date 2020-11-03
DOI 10.1039/D0QO01174F
Impact Factor 5.281
Authors

Zhi-Xin Chang, Jizhong Yan, Chengcai Xia, Fu-Rong Li, Hong-Shuang Li


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Abstract

A rhodium-catalyzed tandem intermolecular hydroacylation of terminal alkyne-substituted secondary alcohols with chelating aldehydes and deconjugative isomerization of the resulting α,β-unsaturated ketones for the preparation of synthetically valuable 1,4-diketones is developed. Of note, the completely atom-economical protocol can be extended to the alkynyl alcohols with appropriate carbon chain length, from which 1,5-diketone and 1,6-diketone were obtained involving the short-range deconjugative isomerization. Given its robustness, broad substrate scope, and excellent regioselectivity, this approach provides a promising platform for the synthesis of diverse diketones.

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
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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

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