Journal
ACS CATALYSIS
Volume 10, Issue 6, Pages 3773-3777Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c00980
Keywords
carbobromination; odd valent nickel; reductive elimination; carbon-bromine bond; alkyne
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Funding
- MEXT (Japan) [18H04253, 17KT0006, 15H05845, 15H03809]
- Council of Human Resources Fostering Program in Chemistry, Japan Chemical Industry Association
- Grants-in-Aid for Scientific Research [18H04253, 17KT0006, 15H03809, 15H05845] Funding Source: KAKEN
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Organohalogen compounds such as alkenyl bromides are versatile and essential building blocks in organic synthesis. Herein, we describe the nickel-catalyzed intermolecular carbobrominations of alkynes with aryl bromides to form highly substituted and functionalized alkenyl bromides. The reductive elimination of the carbon-bromine bond from a Ni(II) species, which is usually a disfavored process, is achieved from a high-valent Ni(III) species in this reaction. This transformation not only expands the scope of transition-metal-complex-promoted bond-forming reactions but also, more particularly, accomplishes the formation of labile bonds, which is as challenging to achieve as the cleavage of inert bonds, such as C-O or C-H bonds.
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