N‐Methylpyrrolidin‐2‐one‐Promoted Formation of Functional Esters through C–O Bond Cleavage. Issue 18 (12th May 2017)

• Record Type: Journal Article
• Authors: Liu, Jianming; Wang, Yanyan; Yue, Yuanyuan; Liu, Na; Zhang, Jian; Zhao, Shufang; Tang, Qinghu; Zhuo, Kelei
• Is Part Of: European journal of organic chemistry. Issue 18(2013)
• Page Start: 2641
• Page End: 2647
• Publication Date: 2017-05-12
• Subjects: Cleavage reactions -- Esterification -- Ethers -- Nucleophilic addition -- Reaction mechanisms; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700514
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Trifluoromethanesulfonic acid catalyzed C–O bond cleavage leading to the preparation of functional esters in the presence of N ‐methylpyrrolidin‐2‐one (NMP) was accomplished. Various substrates were well tolerated, and a gram‐scale experiment was successfully realized. DFT calculations indicated that NMP plays a decisive role in accelerating nucleophilic attack of the functional acid to generate the functional esters in chlorobenzene. Abstract : Trifluoromethanesulfonic acid (HOTf) catalyzed C–O bond cleavage allows the preparation of functional esters in the presence of N ‐methylpyrrolidin‐2‐one (NMP). DFT calculations indicate that NMP plays a decisive role in accelerating nucleophilic attack of the functional acid to generate the ester products in chlorobenzene.