6842-78-0Relevant articles and documents
Selective C-O Bond Reduction and Borylation of Aryl Ethers Catalyzed by a Rhodium-Aluminum Heterobimetallic Complex
Hara, Naofumi,Nakao, Yoshiaki,Saito, Teruhiko,Seki, Rin
, p. 6388 - 6394 (2021/05/31)
We report the catalytic reduction of a C-O bond and the borylation by a rhodium complex bearing an X-Type PAlP pincer ligand. We have revealed the reaction mechanism based on the characterization of the reaction intermediate and deuterium-labeling experiments. Notably, this novel catalytic system shows steric-hindrance-dependent chemoselectivity that is distinct from conventional Ni-based catalysts and suggests a new strategy for selective C-O bond activation by heterobimetallic catalysis.
Light-Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a NiII-Aryl Complex
Cao, Rui,Lai, Chu-Hui,Li, Gang,Liu, Fengyi,Lu, Huan-Huan,Wang, Chao,Xiao, Jianliang,Xue, Dong,Yang, Liu,Zhang, Wei
supporting information, p. 12714 - 12719 (2020/06/02)
A highly effective C?O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is reported. Catalyzed by a NiII-aryl complex under long-wave UV (390–395 nm) irradiation in the presence of a soluble amine base without any additional photosensitizer, the reaction enables the etherification of aryl bromides and aryl chlorides as well as sulfonates with a wide range of primary and secondary aliphatic alcohols, affording synthetically important ethers. Intramolecular C?O coupling is also possible. The reaction appears to proceed via a NiI–NiIII catalytic cycle.
Amine-catalyzed direct photoarylation of unactivated arenes
Zheng, Xingliang,Yang, Luo,Du, Weiyuan,Ding, Aishun,Guo, Hao
supporting information, p. 439 - 442 (2014/02/14)
Constructing biaryls through direct aromatic C-H functionalization of unactivated arenes has become a popular topic in organic chemistry. Many efficient methods have been developed. In this Communication, a direct arylation of unactivated arenes with a broad range of aryl iodides is reported. This reaction proceeds through a new type of amine-catalyzed single electron transfer initiated radical coupling procedure to form biaryls in high yields under UV irradiation at room temperature. Only 20 mol% of TMEDA is used as the catalyst. No other additives are required for this transformation, thus avoiding the use of toxic transition metal catalysts, strong bases, or large amounts of other organic additives. This greener protocol provides a new strategy to achieve direct aromatic C-H functionalization and offers a new example of cost-effective and environmentally benign access to biaryls. Copyright