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Palladium‐Catalyzed Olefination of N ‐Tosylhydrazones as β ‐Diazo Phosphonate Precursors with Arylhalides
Author(s) -
He Jing,
Feng Yijiao,
Yang Fang,
Dai Bin,
Liu Ping
Publication year - 2020
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.202000981
Subject(s) - diazo , chemistry , aryl , phosphonate , palladium , catalysis , halide , combinatorial chemistry , organic chemistry , substrate (aquarium) , alkyl , oceanography , geology
An efficient palladium‐catalyzed olefination of N ‐tosylhydrazones as β ‐diazo phosphonate precursors with aryl halides has been developed. 2,2‐Disubstituted vinylphosphonates bearing versatile functional groups were easily accessed in moderate to excellent yields. Various aryl halides could be employed as the coupling partners, such as (hetero)aryl bromides, aryl iodides, and even aryl chlorides. Moreover, with a similar strategy (2,2‐diphenylvinyl)diarylphosphine oxides can also be attained by the reaction of N ‐tosylhydrazones and aryl bromides. This protocol features easily available raw materials, simple reaction conditions, broad substrate scope as well as scale‐up ability. Moreover, the potential application of this product was exemplified by further transformations.