Palladium-Catalyzed Disilylation and Digermanylation of Alkene Tethered Aryl Halides: Direct Access to Versatile Silylated and Germanylated Heterocycles

Marco Wollenburg; Jonathan Bajohr; Austin D Marchese; Andrew Whyte; Frank Glorius; Mark Lautens

doi:10.1021/acs.orglett.0c01169

Palladium-Catalyzed Disilylation and Digermanylation of Alkene Tethered Aryl Halides: Direct Access to Versatile Silylated and Germanylated Heterocycles

Org Lett. 2020 May 1;22(9):3679-3683. doi: 10.1021/acs.orglett.0c01169. Epub 2020 Apr 20.

Authors

Marco Wollenburg^{1

2}, Jonathan Bajohr², Austin D Marchese², Andrew Whyte², Frank Glorius¹, Mark Lautens²

Affiliations

¹ Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.
² Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.

PMID: 32309953
DOI: 10.1021/acs.orglett.0c01169

Abstract

A method for the palladium-catalyzed disilylation and digermanylation of aryl halides bearing a tethered alkene has been developed. The mechanism is thought to proceed via Heck-type cyclization, followed by C-H activation, resulting in a reactive fused-palladacycle. A wide variety of disilylated and digermanylated heterocycles are obtained from readily available aryl halides in high yields with various functional groups. Moreover, the developed protocol proved to be highly diastereoselective.