Salt-Free Reduction of Transition Metal Complexes by Bis(trimethylsilyl)cyclohexadiene, -dihydropyrazine, and -4,4'-bipyridinylidene Derivatives

Accounts of Chemical Research
Hayato Tsurugi, Kazushi Mashima

Abstract

Chemical reduction of transition metals provides the corresponding low-valent transition metal species as a key step for generating catalytically active species in metal-assisted organic transformations and is a fundamental unit reaction for preparing organometallic complexes. A variety of metal-based reductants, such as metal powders and organometallic reagents of alkali and alkaline-earth metals, have been developed to date to access low-valent metal species. During the reduction, however, reductant-derived metal salts are formed as reaction waste, some of which often interact with the reactive low-valent metal center, thereby disrupting the catalytic performance and hampering the isolation of organometallic complexes as a result of salt coordination to the coordinatively unsaturated vacant and active sites and the formation of thermally unstable ate complexes. In this Account, we emphasize the synthetic utility and versatility of organic reductants containing two trimethylsilyl groups, i.e., 1,4-bis(trimethylsilyl)cyclohexa-2,5-diene (1a) and its methyl derivative (1b), 1,4-bis(trimethylsilyl)dihydropyrazine (2a) and its dimethyl (2b) and tetramethyl (2c) derivatives, and 1,1'-bis(trimethylsilyl)-4,4'-bipyridinylidene (3), l...Continue Reading

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Citations

Jun 6, 2019·Chemical Communications : Chem Comm·Haruka NishiyamaKazushi Mashima
Jan 21, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Daniel M BeaganKenneth G Caulton
Jun 2, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Alyssa C CabelofKenneth G Caulton
Feb 19, 2021·Chemical Communications : Chem Comm·Alyssa C CabelofKenneth G Caulton
Jun 12, 2019·Journal of the American Chemical Society·Sobi AsakoKazuhiko Takai
Apr 5, 2019·Organic Letters·Masahito MuraiKazuhiko Takai
Feb 27, 2020·Inorganic Chemistry·Estefanía Del HornoCarlos Yélamos
Oct 31, 2020·Journal of the American Chemical Society·Rajdip ChowdhuryAbraham Mendoza
Nov 5, 2021·Chemistry : a European Journal·Estefanía Del HornoCarlos Yélamos
Dec 11, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Padmini Sahoo, Moumita Majumdar
Jan 20, 2022·Dalton Transactions : an International Journal of Inorganic Chemistry·Daniel M Beagan, Alyssa C Cabelof

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