Nickel-catalyzed highly chemo- and stereoselective borylative cyclization of 1,6-enynes with bis(pinacolato)diboron

Literature Information

Publication Date 2017-05-17
DOI 10.1039/C7QO00321H
Impact Factor 5.281
Authors

Jen-Chieh Hsieh, Ya-Chun Hong, Chun-Ming Yang, Subramaniyan Mannathan, Chien-Hong Cheng


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Abstract

A highly chemo- and stereoselective nickel-catalyzed borylative cyclization of 1,6-enynes with bis(pinacolato)diboron is described. Enynes containing an electron-deficient alkene such as a vinyl ketone provided alkenylboronates while enynes containing a terminal alkene gave homoallylic boronates. A plausible mechanism involving a nickelacyclopentene intermediate is proposed. In addition, the resulted alkenyl- or homoallylic boronates can be transformed to the corresponding ketones and alcohols via oxidation. Application to a palladium-catalyzed cross coupling reaction of alkenylboronates with aromatic halides has been demonstrated as well.

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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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