Strategic Utilization of Multifunctional Carbene for Direct Synthesis of Carboxylic–Phosphinic Mixed Anhydride from CO2. Issue 52 (28th November 2016)

• Record Type: Journal Article
• Authors: Hoshimoto, Yoichi; Asada, Takahiro; Hazra, Sunit; Kinoshita, Takuya; Sombut, Panukorn; Kumar, Ravindra; Ohashi, Masato; Ogoshi, Sensuke
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 52(2016)
• Page Start: 16075
• Page End: 16079
• Publication Date: 2016-11-28
• Subjects: carbon dioxide fixation -- mixed anhydrides -- N-heterocyclic carbenes -- one-pot reactions -- unsymmetrical ketones; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201609710
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Direct synthesis of carboxylic–phosphinic mixed anhydrides has been achieved by treating carbon dioxide with N‐phosphine oxide‐substituted imidazolylidenes (PoxIms) that contain both nucleophilic carbene and electrophilic phosphorus moieties. This novel mixed anhydride was efficiently derivatized into an ester, an amide, and an unsymmetrical ketone via transformation into its corresponding imidazolium salt followed by a dual substitution reaction. The presented work used well‐designed multifunctional carbene reagents to establish a novel utility for carbon dioxide in organic synthesis. Abstract : CO2 transformation on strategy : Strategic utilization of N ‐phosphine oxide‐substituted imidazolylidenes enabled a direct preparation of a novel carboxylic–phosphinic mixed anhydride from CO2, which was followed by efficient derivatization into a variety of carbonyl compounds.