Work

1-Aminopyridinium Ylides as Monodentate Directing Groups for sp 3 C–H Bond Functionalization

Year: 2019

Type: article

Abstract: 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.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.9b06643

Authors: Ky Khac Anh Le, Hanh Nguyen, Olafs Daugulis

Institution: University of Houston

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Welch Foundation, National Institute of General Medical Sciences

Awards: G4192720128, New Methods for Direct Carbon-Hydrogen Bond Functionalization