Silver‐Catalyzed Cascade Reaction of  N ‐Isocyaniminotriphenylphosphorane with Aldehydes: Synthesis of Unsymmetrical Azines | Zendy

Wang Yeming | Zendy; Yu Yang | Zendy; Zhao Liping | Zendy; Ning Yongquan | Zendy

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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.

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