92495-54-0Relevant articles and documents
Synthesis of Biaryls via Decarbonylative Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Aryl Anhydrides
Zhou, Jing-Ya,Liu, Rui-Qing,Wang, Cheng-Yi,Zhu, Yong-Ming
, p. 14149 - 14157 (2020/11/13)
Transition metal-catalyzed cross-couplings have been widely employed in the synthesis of many important molecules in synthetic chemistry for the construction of diverse C-C bonds. Conventional cross-coupling reactions require active electrophilic coupling partners, such as organohalides or sulfonates, which are not environmentally friendly enough. Herein, we disclose the first nickel-catalyzed Suzuki-Miyaura cross-coupling of aryl anhydrides and arylboronic acids for the synthesis of biaryls in a decarbonylation manner. The reaction tolerates a wide range of electron-withdrawing, electron-neutral, and electron-donating substituents in this process.
Integrating Organic Lewis Acid and Redox Catalysis: The Phenalenyl Cation in Dual Role
Ahmed, Jasimuddin,Chakraborty, Soumi,Jose, Anex,Sreejyothi,Mandal, Swadhin K.
supporting information, p. 8330 - 8339 (2018/06/19)
In recent years, merging different types of catalysis in a single pot has drawn considerable attention and these catalytic processes have mainly relied upon metals. However, development of a completely metal free approach integrating organic redox and organic Lewis acidic property into a single system has been missing in the current literature. This study establishes that a redox active phenalenyl cation can activate one of the substrates by single electron transfer process while the same can activate the other substrate by a donor-acceptor type interaction using its Lewis acidity. This approach has successfully achieved light and metal-free catalytic C-H functionalization of unactivated arenes at ambient temperature (39 entries, including core moiety of a top-selling molecule boscalid), an economically attractive alternative to the rare metal-based multicatalysts process. A tandem approach involving trapping of reaction intermediates, spectroscopy along with density functional theory calculations unravels the dual role of phenalenyl cation.
Rhodium Complexes of 2,6-Bis(dialkylphosphinomethyl)pyridines: Improved C-H Activation, Expanded Reaction Scope, and Catalytic Direct Arylation
Gair, Joseph J.,Qiu, Yehao,Chan, Natalie H.,Filatov, Alexander S.,Lewis, Jared C.
, p. 4699 - 4706 (2018/02/07)
The reactivity of (PNP)Rh(Ph) (PNP = 2,6-bis(dialkylphosphinomethyl)pyridine) toward a variety of electrophiles (Ar-I, ArCH2Cl, O2, I2, B2pin2, and ArSO3H) was explored, and several new modes of oxidative reactivity were observed. Substituting tBu2P for iPr2P provided 100-fold rate enhancement toward C-H bond activation and addressed the previously reported challenge of N2 inhibition. Studying the stoichiometric reactivity of (PNP)Rh complexes toward C-H cleavage and oxidative functionalization led to (PNP)Rh-catalyzed cross-coupling of aryl iodides with sp2 and sp3 C-H bonds.