One-Pot Tandem ortho-Naphthoquinone-Catalyzed Aerobic Nitrosation of N-Alkylanilines and Rh(III)-Catalyzed C-H Functionalization Sequence to Indole and Aniline Derivatives
The nitroso group served as a traceless directing group for the C-H functionalization of N-alkylanilines, ultimately removed after functioning either as an internal oxidant or under subsequent reducing conditions. The unique ability of o-NQ catalysts to aerobically oxidize the N-alkylanilines without using solvents and stoichiometric amounts of oxidants has rendered the new opportunity to develop the telescoped catalyst systems without a need for directly handling the hazardous N-nitroso compounds.
Si, Tengda,Kim, Hun Young,Oh, Kyungsoo
p. 1152 - 1163
(2021/01/14)
A Versatile, Traceless C-H Activation-Based Approach for the Synthesis of Heterocycles
A versatile, traceless C-H activation-based approach for the synthesis of diversified heterocycles is reported. Rh(III)-catalyzed, N-amino-directed C-H alkenylation generates either olefination products or indoles (in situ annulation) in an atom- and step-economic manner at room temperature. The remarkable reactivity endowed by this directing group enables scale-up of the reaction to a 10 g scale at a very low catalyst loading (0.01 mol %/0.1 mol %). Ex situ annulation of olefination product provides entry into an array of heterocycles.
Zhou, Shuguang,Wang, Jinhu,Zhang, Feifei,Song, Chao,Zhu, Jin
supporting information
p. 2427 - 2430
(2016/06/09)
Ruthenium(II)-Catalyzed Traceless C?H Functionalization Using an N?N Bond as an Internal Oxidant
A previously elusive RuII-catalyzed N?N bond-based traceless C?H functionalization strategy is reported. An N-amino (i.e., hydrazine) group is used for the directed C?H functionalization with either an alkyne or an alkene, affording an indole derivative or olefination product. The synthesis features a broad substrate scope, superior atom and step economy, as well as mild reaction conditions.
Zhou, Shuguang,Wang, Jinhu,Chen, Pei,Chen, Kehao,Zhu, Jin
supporting information
p. 14508 - 14512
(2016/10/03)
Rhodium(III)-catalyzed N-nitroso-directed C-H olefination of arenes. High-yield, versatile coupling under mild conditions
N-Nitroso compounds are a versatile class of organic structures that allow expedient access to a diversity of synthetically useful architectures through demonstrated reactivities. We report herein the development of a Rh(III)-catalyzed N-nitroso-directed
Liu, Baoqing,Fan, Yang,Gao, Yang,Sun, Chao,Xu, Cheng,Zhu, Jin
supporting information
p. 468 - 473
(2013/02/23)
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