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Cobalt‐Catalyzed Carbonylation of N ‐Alkylbenzaldimines to ‘ N ‐Alkylphthalimidines’ (= 2,3‐Dihydro‐1 H ‐isoindol‐1‐ones) via Tandem CH Activation and Cyclocarbonylation
Author(s) -
Funk Jeffrey K.,
Yennawar Hemant,
Sen Ayusman
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690167
Subject(s) - chemistry , carbonylation , catalysis , cobalt , carbon monoxide , medicinal chemistry , migratory insertion , aryl , reductive elimination , hydride , tandem , reaction mechanism , ring (chemistry) , stereochemistry , inorganic chemistry , hydrogen , organic chemistry , alkyl , materials science , composite material
The reaction of N ‐alkylbenzaldimines with carbon monoxide (CO) in the presence of cobalt (Co) catalysts resulted in the formation of N ‐alkylphthalimidines ( Table 1 ). Their formation is proposed to occur by CH activation of the aryl ring, migratory insertion of the hydride species into the benzaldimine functionality, CO coordination, and insertion into the CoC bond, followed by reductive elimination of the N ‐alkylphthalimidine and regeneration of the starting Co species ( Scheme 4 ). Deuterium ( 2 H)‐labeling NMR studies are consistent with this mechanism ( Scheme 5 ).