Phosphine-catalyzed 1,2-cis-diboration of 1,3-butadiynes

Weipeng Li; Robert Ricker; Ka Lok Chan; Pak Fung Lau; Nicklas W Buchbinder; Johannes Krebs; Alexandra Friedrich; Zhenyang Lin; Webster L Santos; Udo Radius; Todd B Marder

doi:10.1002/chem.202401235

Phosphine-catalyzed 1,2-cis-diboration of 1,3-butadiynes

Chemistry. 2024 Apr 9:e202401235. doi: 10.1002/chem.202401235. Online ahead of print.

Authors

Affiliations

¹ Nanjing University, School of Chemistry and Chemical Engineering, CHINA.
² Julius-Maximilians-Universitat Wurzburg, Institut für Anorganische Chemie, GERMANY.
³ The Hong Kong University of Science and Technology, Department of Chemistry, HONG KONG.
⁴ Virginia Tech, Department of Chemistry, UNITED STATES.
⁵ Virginia Tech, Dept. of Chemistry, 306 Hahn Hall North, 24061, Blacksburg, UNITED STATES.
⁶ Julius Maximilians University Würzburg, Institut für Anorganische Chemie, Am Hubland, 97074, Würzburg, GERMANY.

PMID: 38593362
DOI: 10.1002/chem.202401235

Abstract

Trialkyl phosphines PMe3 and PEt3 catalyze the 1,2-cis-diboration of 1,3-butadiynes to give 1,2-diboryl enynes. The products were utilized to synthesize 1,1,2,4-tetraaryl enynes using a Suzuki-Miyaura protocol and can readily undergo proto-deborylation.

Keywords: Enyne; boronate ester; cross-coupling; diyne; organocatalysis.