Open AccessDistal Alkenyl C–H Functionalization via the Palladium/Norbornene Cooperative Catalysis
Author(s) -
Weixing Zhao,
Nina Fatuzzo,
Guangbin Dong
Publication year - 2020
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.9b11479
Subject(s) - chemistry , norbornene , palladium , electrophile , catalysis , selectivity , alkylation , surface modification , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , polymerization , polymer
A distal-selective alkenyl C-H arylation method is reported through a directed palladium/norbornene (Pd/NBE) cooperative catalysis. The key is to use an appropriate combination of the directing group and the NBE cocatalyst. A range of acyclic and cyclic cis -olefins are suitable substrates, and the reaction is operated under air with excellent site-selectivity. Preliminary mechanistic studies are consistent with the proposed Pd/NBE-catalyzed C-H activation instead of the Heck pathway. Initial success on distal alkylation has also been achieved using MeI and methyl bromoacetate as electrophiles.