Premium
Catalytic Cascade Access to Biaryl‐2‐Methyl Acetates from Pyruvate O ‐Arylmethyl Ketoximes via the Palladium‐Catalyzed C( sp 2 )H Bond Arylation and C−O Bond Solvolysis
Author(s) -
Shao LingYan,
Xing LiHao,
Guo Ying,
Yu KunKun,
Wang Wei,
Liu HongWei,
Liao DaoHua,
Ji YaFei
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800216
Subject(s) - chemistry , catalysis , palladium , solvolysis , aryl , medicinal chemistry , organic chemistry , stereochemistry , hydrolysis , alkyl
A catalytic cascade has been developed for the synthesis of biaryl‐2‐methyl acetates via a palladium‐catalyzed ortho ‐C( sp 2 )−H bond arylation of pyruvate O ‐arylmethyl ketoximes with aryl iodides followed by a solvolysis, in which the pyruvic ketoxime ester as a new auxiliary is employed to direct the C( sp 2 )−H bond activation. The straightforward treatment of O ‐arylmethyl hydroxylamines and ethyl pyruvate with aryl iodides also provides the target products in a one‐pot fashion. Furthermore, the new palladacycle intermediate is unambiguously confirmed by single‐crystal X‐ray diffraction analysis. A plausible reaction pathway is proposed for the Pd‐catalyzed arylation‐acetolysis sequence.