Photocatalyzed Transition-Metal-Free Oxidative Cross-Coupling Reactions of Tetraorganoborates**
Readily accessible tetraorganoborate salts undergo selective coupling reactions under blue light irradiation in the presence of catalytic amounts of transition-metal-free acridinium photocatalysts to furnish unsymmetrical biaryls, heterobiaryls and arylated olefins. This represents an interesting conceptual approach to forge C?C bonds between aryl, heteroaryl and alkenyl groups under smooth photochemical conditions. Computational studies were conducted to investigate the mechanism of the transformation.
Music, Arif,Baumann, Andreas N.,Boser, Florian,Müller, Nicolas,Matz, Florian,Jagau, Thomas C.,Didier, Dorian
supporting information
p. 4322 - 4326
(2021/02/11)
Electro-Olefination—A Catalyst Free Stereoconvergent Strategy for the Functionalization of Alkenes
Conventional methods carrying out C(sp2)?C(sp2) bond formations are typically mediated by transition-metal-based catalysts. Herein, we conceptualize a complementary avenue to access such bonds by exploiting the potential of electrochemistry in combination with organoboron chemistry. We demonstrate a transition metal catalyst-free electrocoupling between (hetero)aryls and alkenes through readily available alkenyl-tri(hetero)aryl borate salts (ATBs) in a stereoconvergent fashion. This unprecedented transformation was investigated theoretically and experimentally and led to a library of functionalized alkenes. The concept was then carried further and applied to the synthesis of the natural product pinosylvin and the derivatization of the steroidal dehydroepiandrosterone (DHEA) scaffold.
Baumann, Andreas N.,Dechent, Jonas,Didier, Dorian,Jagau, Thomas C.,Müller, Nicolas,Music, Arif
supporting information
(2020/07/04)
Catalytic hydrogen atom transfer (HAT) for sustainable and diastereoselective radical reduction
Going cyclic! A catalytic cycle and cyclic transition states enable a novel sustainable and catalytic hydrogen atom transfer (HAT) for highly diastereoselective radical reductions. Readily available nontoxic silanes are the terminal reductants for epoxides that are opened by bifunctional titanocene(III) hydride catalysts. Copyright
Gansaeuer, Andreas,Klatte, Max,Braendle, Gerhard M.,Friedrich, Joachim
p. 8891 - 8894
(2012/10/08)
Nickel-catalyzed alkenylative cross-coupling reaction of alkyl sulfides
A novel cross-coupling reaction of alkyl aryl sulfides with aryl Grignard reagents has been achieved to produce the alkenyl-aryl coupling products in high yields by using catalytic Ni(cod)2 and a bulky N-heterocyclic carbene ligand, SIPr.
Nickel-catalyzed cross-couplings of cyclohexenyl phosphate and arylboronic acids
The Nickel-catalyzed cross-coupling reaction of cyclohexenylphosphate with a variety of arylboronic acids is described here for the first time. This methodology opens the door to other palladium or nickel-catalyzed coupling reactions involving vinyl phosphates.
Nan, Yang,Yang, Zhen
p. 3321 - 3324
(2007/10/03)
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