173300-93-1Relevant articles and documents
Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction
Becht, Jean-Michel,Catala, Cedric,Le Drian, Claude,Wagner, Alain
, p. 1781 - 1783 (2007)
A simple and efficient route to biaryls via Pd-catalyzed decarboxylative cross-couplings of arene carboxylic acids and aryl iodides is reported. The PdCl2/AsPh3 catalytic system in the presence of Ag 2CO3 in DMS
Evaluation of the Transferability of the “Flexible Steric Bulk” Concept from N-Heterocyclic Carbenes to Planar-Chiral Phosphinoferrocenes and their Electronic Modification
Korb, Marcus,Schaarschmidt, Dieter,Grumbt, Martin,K?nig, Matthias,Lang, Heinrich
supporting information, p. 2968 - 2982 (2020/07/02)
The concept of “flexible steric bulk” is discussed at 2-phenylvinyl-1-phosphinoferrocenes. The introduction of freely rotatable 1'-silyl groups increases the catalytic productivity within the synthesis of tri-ortho-substituted biaryls by Suzuki–Miyaura C,C cross-coupling reactions, giving higher yields with 1/4 of catalyst concentration than for the non-silylated derivatives. Electronic modification of the P and the vinyl donor functionalities was investigated by introducing substituents in the para positions of both groups. Therein, electron-withdrawing phosphines increased the yield from 78 to 91 percent for a given biaryl, by changing from a diphenylphosphino to the P(p-CN-C6H4)2 unit. Opposite results, obtained from electron-donating and sterically demanding phosphines, were in accordance with the 1J(31P,77Se) values. However, the electron density of the ferrocenyl backbone, expressed by the redox potential of the first ferrocenyl-related redox process, cannot be correlated with the donor-properties at the P atom. Changing from a PPh2-substituted ferrocene to a (RA)-1,1'-binaphthyl-containing phosphonite, a complex interaction between the axial- and the planar-chiral motifs occurs, resulting a change of the absolute biaryl configuration.
Murahashi Cross-Coupling at ?78 °C: A One-Pot Procedure for Sequential C?C/C?C, C?C/C?N, and C?C/C?S Cross-Coupling of Bromo-Chloro-Arenes
Sinha, Narayan,Heijnen, Dorus,Feringa, Ben L.,Organ, Michael G.
supporting information, p. 9180 - 9184 (2019/07/04)
The coupling of organolithium reagents, including strongly hindered examples, at cryogenic temperatures (as low as ?78 °C) has been achieved with high-reactivity Pd-NHC catalysts. A temperature-dependent chemoselectivity trigger has been developed for the selective coupling of aryl bromides in the presence of chlorides. Building on this, a one-pot, sequential coupling strategy is presented for the rapid construction of advanced building blocks. Importantly, one-shot addition of alkyllithium compounds to Pd cross-coupling reactions has been achieved, eliminating the need for slow addition by syringe pump.
