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Dual C(sp 3 )−H Bond Functionalization of N‐Heterocycles through Sequential Visible‐Light Photocatalyzed Dehydrogenation/[2+2] Cycloaddition Reactions
Author(s) -
Xu GuoQiang,
Xu JiTao,
Feng ZhiTao,
Liang Hui,
Wang ZhuYin,
Qin Yong,
Xu PengFei
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201710523
Subject(s) - iminium , cycloaddition , dehydrogenation , chemistry , surface modification , bicyclic molecule , vicinal , organocatalysis , enamine , photochemistry , photoredox catalysis , combinatorial chemistry , catalysis , medicinal chemistry , organic chemistry , photocatalysis , enantioselective synthesis
Herein we describe a mild method for the dual C(sp 3 )−H bond functionalization of saturated nitrogen‐containing heterocycles through a sequential visible‐light photocatalyzed dehydrogenation/[2+2] cycloaddition procedure. As a complementary approach to the well‐established use of iminium ion and α‐amino radical intermediates, the elusive cyclic enamine intermediates were effectively generated by photoredox catalysis under mild conditions and efficiently captured by acetylene esters to form a wide array of bicyclic amino acid derivatives, thus enabling the simultaneous functionalization of two vicinal C(sp 3 )−H bonds.