期刊
ORGANIC LETTERS
卷 24, 期 42, 页码 7796-7800出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03135
关键词
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资金
- National Natural Science Foundation of China
- Priority Academic Program Development of the Jiangsu Higher Education Institutes (PAPD)
- [22171200]
A copper-catalyzed reaction for synthesizing diverse alkene/alkyne-containing azepanes through selective functionalization of distal unactivated carbon atoms and broad substrate scope is reported. This reaction allows for late-stage modification of pharmaceuticals and natural products. A radical mechanism involving 1,5-hydrogen atom transfer of N-radicals, facile coupling of alkyl radicals with 1,3-dienes/1,3-enynes, and the construction of azepane motifs via C-N bond formation is proposed.
We herein report a copper-catalyzed formal [5 + 2] aza-annulation of N-fluorosulfonamides and 1,3-dienes/1,3-enynes for synthesis of structurally diverse alkene/alkyne-containing azepanes. The reaction features selective functionalization of distal unactivated C(sp3)-H bonds and a broad substrate scope, thus allowing the late-stage modification of pharmaceuticals and natural products. A radical mechanism involving 1,5-hydrogen atom transfer of N-radicals, facile coupling of alkyl radicals with 1,3-dienes/1,3-enynes, and the construction of azepane motifs via C-N bond formation is proposed.
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