Unknown

Dataset Information

0

1-Aminopyridinium Ylides as Monodentate Directing Groups for sp3 C-H Bond Functionalization.


ABSTRACT: 1-Aminopyridinium ylides are efficient directing groups for palladium-catalyzed ?-arylation and alkylation of sp3 C-H bonds in carboxylic acid derivatives. The efficiency of these directing groups depends on the substitution at the pyridine moiety. The unsubstituted pyridine-derived ylides allow functionalization of primary C-H bonds, while methylene groups are unreactive in the absence of external ligands. 4-Pyrrolidinopyridine-containing ylides are capable of C-H functionalization in acyclic methylene groups in the absence of external ligands, thus rivaling the efficiency of the aminoquinoline directing group. Preliminary mechanistic studies have been performed. A cyclopalladated intermediate has been isolated and characterized by X-ray crystallography, and its reactivity was studied.

SUBMITTER: Le KKA 

PROVIDER: S-EPMC6880753 | BioStudies | 2019-01-01

REPOSITORIES: biostudies

Similar Datasets

2019-01-01 | S-EPMC6892399 | BioStudies
2019-01-01 | S-EPMC6856693 | BioStudies
2019-01-01 | S-EPMC6739411 | BioStudies
2020-01-01 | S-EPMC7744084 | BioStudies
2016-01-01 | S-EPMC5193247 | BioStudies
2019-01-01 | S-EPMC6857669 | BioStudies
1000-01-01 | S-EPMC5433178 | BioStudies
2016-01-01 | S-EPMC5965247 | BioStudies
2016-01-01 | S-EPMC5516954 | BioStudies
2015-01-01 | S-EPMC5659170 | BioStudies