4.7 Article

Platinum-P(BFPy)3-catalyzed regioselective diboration of terminal alkynes with (pin)B-B(aam)

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 5, Pages 1370-1374

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo01903a

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Funding

  1. Tonen General Sekiyu Research/Development Encouragement & Scholarship Foundation
  2. Hiroshima University NOZOMI H Fund Grant for the Promotion of Cancer Research
  3. Fukuoka Naohiko Memorial Foundation
  4. China Scholarship Council (CSC) [202108050140]

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In this study, an unsymmetrical diboron was smoothly added across various terminal alkynes under platinum catalysis, resulting in the regio- and stereoselective formation of cis-vic-diborylalkenes. The use of a highly electron-deficient triarylphosphine ligand, P(BFPy)(3), is crucial for the regiocontrol, and electron deficiency in ligands has been proven to be closely correlated with the regioselectivity.
An unsymmetrical diboron, (pin)B-B(aam), is smoothly added across a carbon-carbon triple bond of various terminal alkynes under platinum catalysis, resulting in the regio- and stereoselective formation of cis-vic-diborylalkenes via B(aam)-installation at the terminal carbon. The use of a highly electron-deficient triarylphosphine ligand, P(BFPy)(3), is indispensable for the regiocontrol, and electron-deficiency in ligands has been proven to be closely correlated with the regioselectivity.

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