Copper Catalysis for Synthesizing Main-Group Organometallics Containing B, Sn or Si

Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]
Hiroto Yoshida

Abstract

A copper complex has proven to be a potent catalyst for forming a C-B bond via diborylation of arynes and alkynes, affording vic-diborylarenes and vic-diborylalkenes with high efficiency. A boryl-substituted organocopper species, which is intermediately generated in the diborylation, has been found to be captured by a tin or a carbon electrophile, leading to three-component borylstannylation or carboboration, in which C-B and C-Sn (or C) bonds are constructed simultaneously. Furthermore, reducing the Lewis acidity of the boron center with 1,8-diaminonaphthalene decisively alters the regiochemical behavior of the borylcopper species, enabling the installation of a boryl moiety to occur at an internal carbon of terminal alkynes in borylstannylation and protoboration. Copper catalysis for C-Sn and C-Si bond-forming processes via distannylation, hydrostannylation and silylstannylation, as well as silver catalysis for a C-B bond-forming reaction, is also described.

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Citations

Jul 20, 2016·Chemical Reviews·Emily C NeeveTodd B Marder
Apr 30, 2017·Chemical Science·Daniel J BlairVarinder K Aggarwal
Oct 19, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yasushi Tsuji, Tetsuaki Fujihara
Aug 3, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Stephen J GeierStephen A Westcott
Jun 3, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Hiroto Yoshida
Feb 6, 2017·Organic Letters·Ikuo KageyukiHiroto Yoshida
Oct 8, 2021·Chemical Reviews·Shubhankar Kumar BoseTodd B Marder
Sep 10, 2021·Chemistry : a European Journal·Dmitriy M VolochnyukOleksandr O Grygorenko

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