Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 18, Pages 11612-11622Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01556
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Funding
- American Chemical Society Petroleum Research Fund [56605-UNI1]
- NIH [1P30 CA-13148, 1510 RR022994-01A1]
- Howard College of Arts and Sciences
- Samford University
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An operationally simple nickel-catalyzed hydroarylation reaction for alkynes is described. This three component coupling reaction utilizes commercially available alkynes and aryl bromides, along with water and Zn. An air-stable and easily synthesized Ni(II) precatalyst is the only entity used in the reaction that is not commercially available. This reductive cross-coupling reaction displays a fairly unusual anti selectivity when aryl bromides with ortho substituents are used. In addition to optimization data and a preliminary substrate scope, complementary experiments including deuterium labeling studies are used to provide a tentative catalytic mechanism. We believe this report should inspire and inform other Ni-catalyzed carbofunctionalization reactions.
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