Rapid Organocatalytic Formation of Carbon Monoxide: Application towards Carbonylative Cross Couplings.

ABSTRACT: Herein, the first organocatalytic method for the transformation of non-derivatized formic acid into carbon monoxide (CO) is introduced. Formylpyrrolidine (FPyr) and trichlorotriazine (TCT), which is a cost-efficient commodity chemical, enable this decarbonylation. Utilization of dimethylformamide (DMF) as solvent and catalyst even allows for a rapid CO generation at room temperature. Application towards four different carbonylative cross coupling protocols demonstrates the high synthetic utility and versatility of the new approach. Remarkably, this also comprehends a carbonylative Sonogashira reaction at room temperature employing intrinsically difficult electron-deficient aryl iodides. Commercial ¹³ C-enriched formic acid facilitates the production of radiolabeled compounds as

SUBMITTER: Zoller B 

PROVIDER: S-EPMC7497008 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature