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Visible Light‐Induced Synthetic Approach for Selenylative Spirocyclization of N ‐Aryl Alkynamides with Molecular Oxygen as Oxidant
Author(s) -
Sahoo Harekrishna,
Mandal Anup,
Dana Suman,
Baidya Mahiuddin
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701410
Subject(s) - chemistry , aryl , visible spectrum , combinatorial chemistry , molecular oxygen , cascade , oxygen , ring (chemistry) , photochemistry , blue light , organic chemistry , optoelectronics , alkyl , physics , chromatography
A visible light‐induced (blue LED) radical cascade has been devised to effect selenylative spirocyclization of N ‐aryl alkynamides at room temperature under oxygen atmosphere and without the aid of external photocatalyst. The protocol is operationally simple, scalable, and offers clean synthesis of 3‐selenospiro[4,5]trienones in high yields (up to 92%). A novel spiro‐ring‐opening strategy has also been accomplished to access fully substituted acryl amides.