Modular radical cross-coupling with sulfones enables access to sp 3 -rich (fluoro)alkylated scaffolds

Abstract

Fluorination is a burgeoning technique for fine-tuning the properties of pharmaceutical compounds. Unfortunately, the cross-coupling reactions widely used to make carbon-carbon bonds in drug research can be tripped up by fluorine substituents. Merchant et al. report a class of easily prepared, solid sulfone compounds that engage in nickel-catalyzed coupling of their fluoroalkyl groups with aryl zinc reagents. These sulfones considerably simplify the synthetic routes to fluorinated analogs that would previously have required multistep strategies focused strictly on the fluorination protocol.

Document Details

Document Type
Pub Defense Publication
Publication Date
Apr 06, 2018
Source ID
10.1126/science.aar7335

Entities

People

  • Cheng Bi
  • Deng-hui Bao
  • Gary M. Gallego
  • Guanda Che
  • Jacob T Edwards
  • James J. Mousseau
  • Lijie Sun
  • Michael R. Collins
  • Monika M. Kruszyk
  • Olugbeminiyi O Fadeyi
  • Phil Baran
  • Philippe Nuhant
  • Rohan R. Merchant
  • Tian Qin
  • Wenhua Qiao

Organizations

  • Innovation Fund Denmark
  • National Institutes of Health
  • Pfizer
  • Scripps Research
  • United States Department of Defense

Tags

Fields of Study

  • Chemistry

Readers

  • Computational Modeling and Simulation
  • Organic Chemistry