Borane-Protecting Strategy for Hydrosilylation of Phosphorus-Containing Olefins

Yuki Naganawa; Akira Fujita; Kei Sakamoto; Shinji Tanaka; Kazuhiko Sato; Yumiko Nakajima

doi:10.1021/acsomega.2c07161

Borane-Protecting Strategy for Hydrosilylation of Phosphorus-Containing Olefins

ACS Omega. 2023 Jan 23;8(6):5672-5682. doi: 10.1021/acsomega.2c07161. eCollection 2023 Feb 14.

Authors

Yuki Naganawa¹, Akira Fujita¹, Kei Sakamoto¹, Shinji Tanaka¹, Kazuhiko Sato¹, Yumiko Nakajima¹

Affiliation

¹ Interdisciplinary Research Center for Catalytic Chemistry (IRC3), National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan.

Abstract

Ir-catalyzed hydrosilylation of the alkenyl phosphine borane complex 1 was achieved to give the corresponding products 2. Because the phosphino group coordinates with metals and is unstable under aerobic conditions, the formation of the corresponding borane adduct was effective not only to promote the target hydrosilylation but also to keep 1 stable under aerobic conditions. The removal of coordinated borane from 2 was readily performed with the treatment by 1,4-diazabicyclo[2.2.2]octane to apply to further transformations. The immobilization and following deprotection of 2 on the surface of mesoporous silica were also examined.