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Cyclocarbonylative Sonogashira Reactions of 1‐Ethynylbenzyl Alcohols: Synthesis of 1‐Carbonylmethylene‐1,3‐Dihydroisobenzofurans
Author(s) -
Aronica Laura Antonella,
Giannotti Luca,
Tuci Giulia,
Zinna Francesco
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.201500539
Subject(s) - chemistry , sonogashira coupling , aryl , stereoselectivity , alcohol , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , palladium , alkyl
In this work, we present a carbonylative Sonogashira reaction of o ‐ethynyl benzyl alcohols and aryl iodides, followed by a cyclization process to selectively give carbonylmethylene isobenzofurans in high yields and in an atom‐economic fashion. The reaction can be carried out in the absence of CuI, with a small amount of PdCl 2 (PPh 3 ) 2 (0.2–0.5 mol‐%), using aryl iodides bearing both electron‐withdrawing and electron‐donating groups. Of the two possible stereoisomeric products, Z ‐isobenzofuran derivatives were obtained as major products. But, when the reaction was extended to a secondary alcohol, an interesting switch in stereoselectivity was observed.