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Silver‐Catalyzed Cascade Reaction of N ‐Isocyaniminotriphenylphosphorane with Aldehydes: Synthesis of Unsymmetrical Azines
Author(s) -
Wang Yeming,
Yu Yang,
Zhao Liping,
Ning Yongquan
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901433
Subject(s) - chemistry , cascade reaction , domino , catalysis , yield (engineering) , intramolecular force , ring (chemistry) , tandem , medicinal chemistry , wittig reaction , combinatorial chemistry , base (topology) , cascade , stereochemistry , organic chemistry , mathematical analysis , materials science , mathematics , metallurgy , composite material , chromatography
A direct synthesis of azines from the silver catalyzed domino interaction of N ‐isocyaniminotriphenylphosphorane and aldehydes is reported. The reaction proceeds through a tandem aza ‐Wittig, insertion, intramolecular cyclization and ring‐opening processes. The use of DIPEA as a base and BF 3 · Et 2 O as an additive significantly enhance the yield of a range of unsymmetrical azines.