A versatile iodo(III)etherification of terminal ethynylsilanes using BF3-OiPr2 and alkyl benzyl ethers

Takuya Matsumoto; Hiroshi Hagiyama; Kanetsugu Kuribayashi; Kazuhito Hioki; Hikaru Fujita; Masahito Ochiai; Munetaka Kunishima

doi:10.1039/d1ob00479d

A versatile iodo(III)etherification of terminal ethynylsilanes using BF₃-OⁱPr₂ and alkyl benzyl ethers

Org Biomol Chem. 2021 May 5;19(17):3825-3828. doi: 10.1039/d1ob00479d.

Authors

Takuya Matsumoto¹, Hiroshi Hagiyama², Kanetsugu Kuribayashi¹, Kazuhito Hioki², Hikaru Fujita¹, Masahito Ochiai³, Munetaka Kunishima¹

Affiliations

¹ Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. kunisima@p.kanazawa-u.ac.jp.
² Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 Minatojima, Chuo-ku, Kobe 650-8586, Japan.
³ Graduate School of Pharmaceutical Sciences, Tokushima University, 1-78 Shomachi, Tokushima 770-8505, Japan.

PMID: 33949597
DOI: 10.1039/d1ob00479d

Abstract

A series of (E)-α-silyl-β-alkoxyvinyl-λ3-iodanes was synthesized from iodosylbenzene, BF3-ether complexes, and terminal ethynylsilanes. The combined use of BF3-OiPr2 and benzyl ethers of primary alcohols (ROBn) allows the chemoselective transfer of primary alkoxy groups (RO) onto the β-position of the terminal ethynylsilanes.