Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 23, Pages 5383-5391Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201900819
Keywords
Selective inside-outside C-N bond cleavage; N-acylisatins; coupling; transamination; multipurpose reagents
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Funding
- Science and Technology Planning Project of Guangdong Province [2017A010103017]
- National Natural Science Foundation of China [51703069, 21272080]
- Special Innovation Projects of Common Universities in Guangdong Province [20178S0182]
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New multipurpose arylation/acylation/transamination reagents, N-acylisatins, have been developed by selective 'inside-outside' C-N bond cleavage under different catalytic conditions. As activated amides, N-acylisatins undergo Rh-catalyzed C-H arylation and Pd-catalyzed acylation by cleavage outside the C-N bond, and the desired biaryls and diaryl ketones were obtained in good to excellent yields. Generally, the combination of N-acylisatins with amines leads to a ring-opening reaction and formation of transamination products in a predictable manner through inside C-N bond cleavage. Interestingly, treatment of N-acylisatins with amines lead to unexpected outer-ring transamination products when CsF is added, which shows that CsF can favor the outside C-N bond cleavage path. Notably, this work presents a new strategy for multiple chemical transformations of a single amide to achieve various products by selective C-N bond cleavage.
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