Et3SiH + KO: T Bu provide multiple reactive intermediates that compete in the reactions and rearrangements of benzylnitriles and indolenines
The combination of potassium tert-butoxide and triethylsilane is unusual because it generates multiple different types of reactive intermediates simultaneously that provide access to (i) silyl radical reactions, (ii) hydrogen atom transfer reactions to cl
Arokianathar, Jude N.,Clark, Kenneth F.,Dimitrova, Daniela,Leach, Stuart G.,Murphy, John A.,Poole, Darren L.,Smith, Andrew J.
p. 12364 - 12370
(2020/12/08)
Room Temperature Catalyst System for the Hydroarylation of Olefins
A simple protocol for the hydroarylation of olefins to yield diarylmethine products is described. A Friedel-Crafts-type synthetic strategy allows direct access to biorelevant products in high atom efficiency. A combination of substoichiometric amounts of TMSCl and ZnBr2 promotes a rapid hydroarylation process at ambient temperature. The method is high yielding and is amenable to scale-up protocols.
Lee, Siu Yin,Villani-Gale, Alexander,Eichman, Chad C.
supporting information
p. 5034 - 5037
(2016/10/14)
Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Alkyl Bromides: Et3N as the Terminal Reductant
Reductive cross-coupling has emerged as a direct method for the construction of carbon-carbon bonds. Most cobalt-, nickel-, and palladium-catalyzed reductive cross-coupling reactions to date are limited to stoichiometric Mn(0) or Zn(0) as the reductant. One nickel-catalyzed cross-coupling paradigm using Et3N as the terminal reductant is reported. By using this photoredox catalysis and nickel catalysis approach, a direct Csp2-Csp3 reductive cross-coupling of aryl bromides with alkyl bromides is achieved under mild conditions without stoichiometric metal reductants.
Duan, Zhengli,Li, Wu,Lei, Aiwen
supporting information
p. 4012 - 4015
(2016/08/30)
Highly efficient gold(III)-catalyzed intermolecular hydroarylation of unactivated alkenes with arenes under mild conditions
A simple and efficient method for functionalization of electron-rich arenes and heteroarenes with unactivated alkenes by Au(III)-catalyzed intermolecular hydroarylation under mild reaction conditions was developed. This method features a short reaction time (5 h) under mild conditions and has a broad substrate scope, including electron-rich arenes and heteroarenes, terminal and internal substituted aryl alkenes, and unactivated aliphatic alkenes.
Xiao, Ya-Ping,Liu, Xin-Yuan,Che, Chi-Ming
experimental part
p. 494 - 501
(2009/06/06)
Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides-reaction discovery using parallel microscale experimentation
Microscale parallel experimentation was used to discover three catalyst systems capable of coupling secondary organotrifluoroborates with sterically and electronically demanding aryl chlorides and bromides. The ensuing results represent the first comprehensive study of alkylboron coupling to aryl chlorides and, in particular, using secondary alkylboron partners. A ligand-dependent β-hydride elimination/reinsertion mechanism was implicated in the cross-coupling of more hindered substrates, leading to isomeric mixtures of coupled products in some cases. Copyright
Dreher, Spencer D.,Dormer, Peter G.,Sandrock, Deidre L.,Molander, Gary A.
supporting information; body text
p. 9257 - 9259
(2009/02/02)
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