Catalyst-Free and Regioconvergent Substitution Reactions of Bromothiophenes with a BH3-Substituted Phosphide Anion

Tsuneo Imamoto; Yumi Horiuchi; Ken Tamura; Masashi Sugiya; Hyuma Masu

doi:10.1021/acs.orglett.6b02094

Catalyst-Free and Regioconvergent Substitution Reactions of Bromothiophenes with a BH3-Substituted Phosphide Anion

Org Lett. 2016 Aug 19;18(16):4132-5. doi: 10.1021/acs.orglett.6b02094. Epub 2016 Aug 10.

Authors

Tsuneo Imamoto^{1

2}, Yumi Horiuchi¹, Ken Tamura¹, Masashi Sugiya¹, Hyuma Masu³

Affiliations

¹ Organic R&D Department, Nippon Chemical Industrial Co., Ltd. , Kameido, Koto-ku, Tokyo, 136-8515, Japan.
² Department of Chemistry, Graduate School of Science, Chiba University , Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
³ Center for Analytical Instrumentation, Chiba University , Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.

PMID: 27509360
DOI: 10.1021/acs.orglett.6b02094

Abstract

A range of bromothiophenes reacted with lithium boranato(tert-butyl)methylphosphide in the absence of transition-metal catalysts under mild conditions to provide the same 2,5-disubstituted and 2-monosubstituted products regardless of the substitution patterns of the starting bromothiophenes.