Transition-Metal-Free Thioboration of Terminal Alkynes

Taro Matsuyama; Hiroshi Ishida; Chao Wang; Kazunori Miyamoto; Masaya Nakajima; Naoyuki Toriumi; Yuki Nagashima; Masanobu Uchiyama

doi:10.1021/jacsau.4c00907

Transition-Metal-Free Thioboration of Terminal Alkynes

JACS Au. 2024 Nov 15;4(12):4927-4933. doi: 10.1021/jacsau.4c00907. eCollection 2024 Dec 23.

Authors

Taro Matsuyama¹, Hiroshi Ishida¹, Chao Wang², Kazunori Miyamoto^{1

3}, Masaya Nakajima¹, Naoyuki Toriumi¹, Yuki Nagashima¹, Masanobu Uchiyama^{1

4}

Affiliations

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
² Faculty of Pharmaceutical Sciences, Institute of Medicinal, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa-shi, Ishikawa 920-1192, Japan.
³ Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan.
⁴ Research Initiative for Supra-Materials (RISM), Shinshu University, 3-15-1 Tokida, Ueda, Nagano 386-8567, Japan.

Abstract

We present a new type of elementoboration reaction, the thioboration of terminal alkynes. This method enables highly controllable regio-/stereo-/chemoselective cis- and trans-thioboration on demand, affording synthetically versatile and densely functionalized vinyl boron/vinyl sulfide derivatives in a straightforward manner without the need for a transition-metal catalyst.