Work

In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides

Year: 2015

Type: article

Abstract: A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is C-F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing phenyl groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.

Source: Organometallics

DOI: 10.1021/acs.organomet.5b00631

Authors: Phillip J. Milner, Yang Yang, Stephen L. Buchwald

Institutions: Massachusetts Institute of Technology, University of Pittsburgh

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: National Science Foundation, Amgen, National Institute of General Medical Sciences