A novel strategy for the catalytic synthesis of 2-aryl-2-benzo[][1,2,3]triazoles bearing a wide range of functional groups in good to excellent yields by non-noble molybdenum-catalyzed deoxygenative heterocyclization of 2-nitroazobenzenes is described. The salient features of the transformation include the use of readily available substrates, valuable products and ease of scale-up. The mechanistic study indicates that the reaction occurred double deoxygenation by the Mo(VI)/Mo(IV) catalytic cycle from 2-nitroazobenzene, through the formation of 2-aryl-2-benzo[][1,2,3]triazole--oxide or nitrene intermediates.
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Molybdenum-catalyzed deoxygenative heterocyclization of 2-nitroazobenzenes: a novel strategy for catalytic synthesis of 2-aryl-2-benzo[][1,2,3]triazoles.
Org Biomol Chem
January 2024
School of Pharmacy, Changzhou University, Changzhou, Jiangsu Province 213164, China.
A novel strategy for the catalytic synthesis of 2-aryl-2-benzo[][1,2,3]triazoles bearing a wide range of functional groups in good to excellent yields by non-noble molybdenum-catalyzed deoxygenative heterocyclization of 2-nitroazobenzenes is described. The salient features of the transformation include the use of readily available substrates, valuable products and ease of scale-up. The mechanistic study indicates that the reaction occurred double deoxygenation by the Mo(VI)/Mo(IV) catalytic cycle from 2-nitroazobenzene, through the formation of 2-aryl-2-benzo[][1,2,3]triazole--oxide or nitrene intermediates.
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Angew Chem Int Ed Engl
July 2021
State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, P. R. China.
The transition-metal-catalyzed cyclopropanation of alkenes by the decomposition of diazo compounds is a powerful and straightforward strategy to produce cyclopropanes, but is tempered by the potentially explosive nature of diazo substrates. Herein we report the Mo-catalyzed regiospecific deoxygenative cyclopropanation of readily available and bench-stable 1,2-dicarbonyl compounds, in which one of the two carbonyl groups acts as a carbene equivalent upon deoxygenation and engages in the subsequent cyclopropanation process. The use of a commercially available Mo catalyst afforded an array of valuable cyclopropanes with exclusive regioselectivity in up to 90 % yield.
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Chemistry
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State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Dalian National Laboratory for Clean Energy, Dalian, 116023, P. R. China.
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