Copper-Catalyzed Stereospecific Transformations of Alkylboronic Esters
Ningxin Xu, Hao Liang, and James P. Morken*
*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States,
Email: morken
bc.edu
N. Xu, H. Liang, J. P. Morken, J. Am. Chem. Soc., 2022, 144, 11546-11552.
DOI: 10.1021/jacs.2c04037
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Abstract
Boron "ate" complexes derived from pinacol boronic esters and tert-butyl lithium undergo stereospecific transmetalation to copper cyanide, followed by coupling with alkynyl bromides, allyl halides, propargylic halides, β-haloenones, hydroxylamine esters, and acyl chlorides. This simple transformation converts primary and secondary alkylboronic esters to a wide array of useful compounds.
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proposed reaction pathway
Key Words
alkynylation, allylation, allenes
ID: J48-Y2022
