Reductive anti-Dizincation of Arylacetylenes

Haruka Yamaguchi; Fumiya Takahashi; Takashi Kurogi; Hideki Yorimitsu

doi:10.1002/asia.202400384

Reductive anti-Dizincation of Arylacetylenes

Chem Asian J. 2024 Apr 22:e202400384. doi: 10.1002/asia.202400384. Online ahead of print.

Authors

Haruka Yamaguchi¹, Fumiya Takahashi¹, Takashi Kurogi¹, Hideki Yorimitsu²

Affiliations

¹ Kyoto University, Chemistry, JAPAN.
² Kyoto University: Kyoto Daigaku, Department of Chemistry, Graduate School of Science, Sakyo-ku, 606-8502, Kyoto, JAPAN.

PMID: 38647096
DOI: 10.1002/asia.202400384

Abstract

Arylacetylenes undergo anti-1,2-dizincation to afford trans-1,2-dizincioalkenes. The process employs sodium dispersion as a reducing agent and zinc chloride TMEDA complex as a reduction-resistant zinc electrophile. This reductive anti-dizincation contrasts with the conventional additive syn-dimetalation like silylzincation. The resulting dizincated alkenes undergo the cross-coupling to yield multi-substituted alkenes stereoselectively.

Keywords: 1,2-Dizincioalkene; Dizincation; Reduction; Sodium; Zinc.