Regiospecific synthesis of distally chlorinated ketones via C–C bond cleavage of cycloalkanols

Literature Information

Publication Date 2015-12-10
DOI 10.1039/C5QO00368G
Impact Factor 5.281
Authors

Xuefeng Fan, Huijun Zhao, Jiajia Yu, Xiaoguang Bao


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Abstract

A variety of distally Csp3-chlorinated ketones are synthesized with good regioselectivities via silver-catalyzed ring opening of cycloalkanols under mild reaction conditions. The reaction uses only routine, inexpensive reagents and can be scaled up to gram quantities. A novel radical-mediated C–C bond cleavage/C–Cl bond formation is proposed.

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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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