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
View Original
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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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
Recommended Compounds
N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyrimidinamine
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1032759-30-0
Molecular Formula:
C12H20BN3O2
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(2S)-2-{[(9H-Fluoren-9-ylmethoxy)carbonyl]amino}-4-(methylselanyl)butanoic acid
CAS Number:
1217852-49-7
Molecular Formula:
C20H21NO4Se
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