Pd‐Catalyzed MIA‐Directed Acetoxylation of Benzylamines and Computational Study. Issue 37 (5th October 2022)

• Record Type: Journal Article
• Authors: Meng, Yue‐Ning; Zhao, Shi‐Chen; Liu, Peng‐Yu; Hu, Dianwen; Wang, Shuai; He, Yu‐Peng; Yu, Fang
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 37(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-10-05
• Subjects: Acetoxylation -- Benzylamines -- C−H functionalization -- Methoxyiminoacyl -- Pd-catalyzed; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200728
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The direct acetoxylation of substituted benzylamines has been accomplished through methoxyiminoacyl (MIA)‐mediated Pd‐catalyzed C−H functionalization. A diverse array of phenylalanine substrates is amenable to this protocol, providing acetoxylation benzylamine derivatives with good to high efficiency. Computational results revealed that HOAc enhanced the stability of Pd−O bond, which obviously accelerate the reductive elimination step of the acetoxylation process. Abstract : A highly efficient MIA‐mediated acetoxylation of substituted benzylamines was reported, which tolerate various substituent groups with good to high yields. DFT‐Studies showed that a weaker electrostatic attraction of HOAc to OAc led to the preferential formation of a five‐membered cyclopalladium intermediate (OAc−Pd−C).