Palladium-Catalyzed Carbonylation of Aryl Iodides with Sulfinamides

A facile palladium(0)‐catalyzed carbonylative protocol for the generation of new acyl‐sulfinamides in moderate to good yields is described. Aliphatic and aromatic sulfinamides were exploited as hitherto unexplored nucleophiles in carbonylation chemistry, with use of CO gas generated ex situ from Mo(...

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Bibliographic Details
Published in:European journal of organic chemistry 2015-11, Vol.2015 (32), p.7069-7074
Main Authors: Belfrage, Anna Karin, Wakchaure, Prasad, Larhed, Mats, Sandström, Anja
Format: Article
Language:English
Subjects:
Carbonylation
Homogenous catalysis
Molybdenum
Palladium
Sulfinamides
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Summary:A facile palladium(0)‐catalyzed carbonylative protocol for the generation of new acyl‐sulfinamides in moderate to good yields is described. Aliphatic and aromatic sulfinamides were exploited as hitherto unexplored nucleophiles in carbonylation chemistry, with use of CO gas generated ex situ from Mo(CO)6 in a sealed two‐chamber system. Both electron‐poor and electron‐rich (hetero)aryl iodides were employed as electrophiles. The two‐chamber system and the use of an inorganic base were essential for efficacious synthesis of acyl‐sulfinamide products. Finally, it was demonstrated that a one‐pot (or single‐vial) synthesis of acyl‐sulfinamides was feasible under CO at balloon pressure in the presence of Cs2CO3 as base. Easy access to the multifunctional acyl‐sulfinamide functionality is demonstrated. Sulfinamides have been explored as new nucleophiles in carbonylation chemistry and have yielded various acyl‐sulfinamides from aryl iodides in a two‐compartment system for CO generation.
ISSN:1434-193X
1099-0690
1099-0690
DOI:10.1002/ejoc.201500875