Diverse Synthesis of Alkenylsilanes via Pd-Catalyzed Alkenyl C-H Silylation

Zi-Hang Ye; Fei-Hu Gou; Yichen Wu; Chuan-Ying Li; Peng Wang

doi:10.1021/acs.orglett.3c00633

Diverse Synthesis of Alkenylsilanes via Pd-Catalyzed Alkenyl C-H Silylation

Org Lett. 2023 Mar 31;25(12):2145-2150. doi: 10.1021/acs.orglett.3c00633. Epub 2023 Mar 15.

Authors

Zi-Hang Ye^{1

2}, Fei-Hu Gou², Yichen Wu², Chuan-Ying Li¹, Peng Wang^{2

3

4}

Affiliations

¹ Department of Chemistry, Key Laboratory of Surface and Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Xiasha West Higher Education District, Hangzhou 310018, P. R. China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, P. R. China.
³ CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, P. R. China.
⁴ School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou 310024, P. R. China.

PMID: 36921249
DOI: 10.1021/acs.orglett.3c00633

Abstract

Here, we disclose a general approach for the diverse synthesis of alkenylsilanes in a highly efficient, stereoselective, and atom-economic manner by leveraging the palladium-catalyzed disilylation reaction of 2-bromostyrene derivatives with hexamethyldisilane, which is suitable for the preparation of a series of disubstituted, trisubstituted, and tetrasubstituted alkenylsilanes. Furthermore, the resulting tetrasubstituted alkenylsilanes could be readily transformed into the corresponding diarylated benzosiloles, which have been proven to be a potential AIE material and a fluorene material.