Journal
ORGANIC LETTERS
Volume 20, Issue 3, Pages 864-867Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b04029
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Funding
- National Natural Science Foundation of China (NSFC) [21702050, 21572047]
- Program for Innovative Research Team in Science and Technology in Universities of Henan Province [15IRTSTHN003]
- Program for Science and Technology Innovation Talents in Universities of Henan Province [15HASTIT005]
- Plan for Scientific Innovation Talents of Henan Province [184200510012]
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A novel synthesis of pyrrolidine-2-carbaldehydes or tetrahydropyridine-2-carbaldehydes from the cascade reactions of N-arylpiperidines or N-arylazepanes is presented. Mechanistically, the formation of the title compounds involves an unprecedented oxidative ring contraction of inactivated cyclic amines via Cu(OAc)(2)/KI/O-2-promoted oxidative cleavage and reformation of the C-N bond. Interestingly, when PhI(OAc)(2) was used in place of KI, 1,1-diacetates of the corresponding aldehydes were directly obtained with good efficiency. To the best of our knowledge, this is the first example of regioselective C(sp(3))-H bond functionalization and C(sp(3))-N bond activation of saturated cyclic amines using copper salt and oxygen.
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