Premium
Rh III ‐Catalyzed Olefination of 2‐Aryloxypyridines Using 2‐Pyridyloxyl as the Removable Directing Group
Author(s) -
Borah Arun Jyoti,
Yan Guobing,
Wang Lianggui
Publication year - 2015
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.201500530
Subject(s) - chemistry , catalysis , acrylamide , acrylate , phenol , solvent , organic chemistry , coupling reaction , medicinal chemistry , copolymer , polymer
An efficient Rh III ‐catalyzed trans selective ortho ‐olefination of 2‐aryloxypyridines has been developed. The catalytic system is very effective for olefination of differently substituted 2‐aryloxypyridines with acrylates, acrylamide and styrenes and exhibits broad compatibility with assorted olefinic coupling partners. Although acrylates and acrylamide give rise to trans ‐olefinated products in MeOH, styrenes provided the trans products under solvent free reaction conditions. Interestingly, in olefinations with ethyl acrylate, the aryloxypyridine compound bearing keto functionality at the ortho position was found to undergo directing group cleavage to afford the olefinated phenol product directly.