Oxidative Addition of Aryl Tosylates to Palladium(0) and Coupling of Unactivated Aryl Tosylates at Room Temperature

2003 ◽  
Vol 125 (29) ◽  
pp. 8704-8705 ◽  
Author(s):  
Amy H. Roy ◽  
John F. Hartwig
Keyword(s):  
Room Temperature ◽  
Oxidative Addition ◽  
Aryl Tosylates

scholarly journals Si–C(sp3) bond activation through oxidative addition at a Rh(i) centre

2020 ◽  
Vol 49 (17) ◽  
pp. 5416-5419
Author(s):  
S. Azpeitia ◽  
A. J. Martínez-Martínez ◽  
M. A. Garralda ◽  
A. S. Weller ◽  
M. A. Huertos
Keyword(s):  
Room Temperature ◽  
Bond Activation ◽  
Oxidative Addition

Rhodium promoted a fast, quantitative and room temperature Si–CH3 bond activation.

scholarly journals Ring expansion of a ring expanded carbene

2017 ◽  
Vol 46 (36) ◽  
pp. 12015-12018 ◽  
Author(s):  
Lucía García ◽  
Khalidah H. M. Al Furaiji ◽  
David J. D. Wilson ◽  
Jason L. Dutton ◽  
Michael S. Hill ◽  
...  
Keyword(s):  
Ring Opening ◽  
Room Temperature ◽  
Oxidative Addition ◽  
Ring Expansion

Reaction of phenylsilane with the ring expanded carbene 6-Mes results in facile Si–H oxidative addition to the carbenic carbon at room temperature and ring opening on heating.

Oxidative Addition of a Strained C–C Bond onto Electron-Rich Rhodium(I) at Room Temperature

2013 ◽  
Vol 135 (19) ◽  
pp. 7142-7145 ◽  
Author(s):  
Yusuke Masuda ◽  
Maki Hasegawa ◽  
Makoto Yamashita ◽  
Kyoko Nozaki ◽  
Naoki Ishida ◽  
...  
Keyword(s):  
Room Temperature ◽  
Oxidative Addition

Oxidative addition reactions of benzo[b]thiophene and dibenzothiophene with [Os3(CO)10(MeCN)2]: room-temperature ring opening of benzo[b]thiophene at triosmium clusters

1999 ◽  
Vol 285 (2) ◽  
pp. 277-282 ◽  
Author(s):  
Alejandro J. Arce ◽  
Arquı́medes Karam ◽  
Ysaura De Sanctis ◽  
Mario V. Capparelli ◽  
Antony J. Deeming
Keyword(s):  
Ring Opening ◽  
Room Temperature ◽  
Oxidative Addition ◽  
Addition Reactions ◽  
Triosmium Clusters

C(sp2)–C(sp2) Reductive Elimination from a Diarylplatinum(II) Complex Induced by a S–S Bond Oxidative Addition at Room Temperature

2020 ◽  
Vol 39 (3) ◽  
pp. 417-424 ◽  
Author(s):  
Hamid R. Shahsavari ◽  
Reza Babadi Aghakhanpour ◽  
Abbas Biglari ◽  
Maryam Niazi ◽  
Piero Mastrorilli ◽  
...  
Keyword(s):  
Room Temperature ◽  
Oxidative Addition ◽  
Reductive Elimination

scholarly journals HARC as an open-shell strategy to bypass oxidative addition in Ullmann–Goldberg couplings

2020 ◽  
Vol 117 (35) ◽  
pp. 21058-21064
Author(s):  
Marissa N. Lavagnino ◽  
Tao Liang ◽  
David W. C. MacMillan
Keyword(s):  
Room Temperature ◽  
Elevated Temperatures ◽  
Large Range ◽  
Aryl Halide ◽  
Oxidative Addition ◽  
Open Shell ◽  
Bond Forming ◽  
Aryl Bromides ◽  
Sterically Demanding ◽  
Rapid Diversification

The copper-catalyzed arylation of unsaturated nitrogen heterocycles, known as the Ullmann–Goldberg coupling, is a valuable transformation for medicinal chemists, providing a modular disconnection for the rapid diversification of heteroaromatic cores. The utility of the coupling, however, has established limitations arising from a high-barrier copper oxidative addition step, which often necessitates the use of electron-rich ligands, elevated temperatures, and/or activated aryl electrophiles. Herein, we present an alternative aryl halide activation strategy, in which the critical oxidative addition (OA) mechanism has been replaced by a halogen abstraction–radical capture (HARC) sequence that allows the generation of the same Cu(III)-aryl intermediate albeit via a photoredox pathway. This alternative mechanistic paradigm decouples the bond-breaking and bond-forming steps of the catalytic cycle to enable the use of many previously inert aryl bromides. Overall, this mechanism allows access to both traditional C–N adducts at room temperature as well as a large range of previously inaccessible Ullmann–Goldberg coupling products including sterically demandingortho-substituted heteroarenes.

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