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Stereoselective Synthesis of ( E )‐3‐(Methoxycarbonyl)methylene‐1,3‐dihydroindol‐2‐ones by Palladium‐Catalyzed Oxidative Carbonylation of 2‐Ethynylanilines
Author(s) -
Gabriele Bartolo,
Salerno Giuseppe,
Veltri Lucia,
Costa Mirco,
Massera Chiara
Publication year - 2001
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 - 10.1002/1099-0690(200112)2001:24<4607::aid-ejoc4607>3.0.co;2-d
Subject(s) - chemistry , carbonylation , palladium , catalysis , methylene , oxidative phosphorylation , stereoselectivity , medicinal chemistry , solvent , oxidative addition , triple bond , organic chemistry , stereochemistry , double bond , carbon monoxide , biochemistry
A direct synthesis of ( E )‐3‐(methoxycarbonyl)methylene‐1,3‐dihydroindol‐2‐ones 2 by palladium‐catalyzed oxidative carbonylation of 2‐ethynylanilines 1 is reported. Reactions were carried out in MeOH as the solvent at 50−70 °C in the presence of catalytic amounts of PdI 2 in conjunction with KI under a 4:1 CO/air mixture (20 atm total pressure at 25 °C). When the reaction was applied to 2‐alkynylanilines with internal triple bonds, the reaction course changed completely, with formation of carbamates 4 .