Open AccessAn Electroreductive Approach to Radical Silylation via the Activation of Strong Si–Cl Bond
Author(s) -
Lingxiang Lu,
Juno C. Siu,
Yihuan Lai,
Song Lin
Publication year - 2020
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.0c10899
Subject(s) - silylation , chemistry , hydrosilylation , alkene , radical , allylic rearrangement , transition metal , context (archaeology) , electrochemistry , bond cleavage , medicinal chemistry , photochemistry , organic chemistry , catalysis , electrode , paleontology , biology
The construction of C(sp 3 )-Si bonds is important in synthetic, medicinal, and materials chemistry. In this context, reactions mediated by silyl radicals have become increasingly attractive but methods for accessing these intermediates remain limited. We present a new strategy for silyl radical generation via electroreduction of readily available chlorosilanes. At highly biased potentials, electrochemistry grants access to silyl radicals through energetically uphill reductive cleavage of strong Si-Cl bonds. This strategy proved to be general in various alkene silylation reactions including disilylation, hydrosilylation, and allylic silylation under simple and transition-metal-free conditions.