Premium
Pd‐Catalyzed C(sp 2 )−H Alkoxycarbonylation of Phenethyl‐ and Benzylamines with Chloroformates as CO Surrogates
Author(s) -
AndradeSampedro Paula,
Matxain Jon M.,
Correa Arkaitz
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202005338
Subject(s) - chemistry , catalysis , carbon monoxide , combinatorial chemistry , functional group , carbonylation , density functional theory , catalytic cycle , molecule , organic chemistry , computational chemistry , polymer
The site‐selective functionalization of C−H bonds within a complex molecule remains a challenging task of capital synthetic importance. Herein, an unprecedented Pd‐catalyzed C(sp 2 )−H alkoxycarbonylation of phenylalanine derivatives and other amines featuring picolinamide as the directing group (DG) is reported. This oxidative coupling is distinguished by its scalability, operational simplicity, and avoids the use of toxic carbon monoxide as the C 1 source. Remarkably, the easy cleavage of the DG enables the efficient assembly of isoindolinone compounds. Density Functional Theory calculations support a Pd II /Pd IV catalytic cycle.