Results
Title

Iron‐Catalyzed Regioselective Alkenylboration of Olefins.

Authors

Yu, Xiaolong; Zheng, Hongling; Zhao, Haonan; Lee, Boon Chong; Koh, Ming Joo

Abstract

The first examples of an iron‐catalyzed three‐component synthesis of homoallylic boronates from regioselective union of bis(pinacolato)diboron, an alkenyl halide (bromide, chloride or fluoride), and an olefin are disclosed. Products that bear tertiary or quaternary carbon centers could be generated in up to 87 % yield as single regioisomers with complete retention of the olefin stereochemistry. With cyclopropylidene‐containing substrates, ring cleavage leading to trisubstituted E‐alkenylboronates were selectively obtained. Mechanistic studies revealed reaction attributes that are distinct from previously reported alkene carboboration pathways.

Subjects

STEREOCHEMISTRY; FLUORIDES; HALIDES; BROMIDES; CHLORIDES; ALKENES; IRON chlorides; ALKENYL group

Publication

Angewandte Chemie, 2021, Vol 133, Issue 4, p2132

ISSN

0044-8249

Publication type

Academic Journal

DOI

10.1002/ange.202012607