.
1H NMR

 Compounds containing a sulfur–fluoride bond are receiving escalating attention in both the chemical and the biological literature. The need to activate the S–F bond through formation of a hydrogen bond in the presence of a proximal nucleophile forms the basis for sulfonyl fluorides to be utilized as privileged biocompatible orthogonal electrophiles in biological systems. Arvidsson at the Karolinska Institute and his co-workers at the University of KwaZulu-Natal reported an efficient, ligand-free, and additive free Suzuki–Miyaura coupling that is compatible with an aromatic sulfonyl fluoride moiety ( J. Org. Chem. 2016, 81, 2618). After extensive optimization studies, mild reaction conditions were identified that minimized hydrolysis of the aromatic sulfonyl fluoride. Palladium acetate was the most effective catalyst, and utilization of triethylamine as the base afforded the highest yield. The reaction was conducted in water as solvent, at room temperature. These mild reaction conditions were compatible with a variety of functional groups on the boronic acid, including: nitro, chloro, fluoro, nitrile, and ethers. The desired biaryl sulfonyl fluorides were obtained in good-to-excellent yields.

19 F NMR

.

On-Water Synthesis of Biaryl Sulfonyl Fluorides

Praveen K. Chinthakindi^†, Hendrik G. Kruger^†, Thavendran Govender^†, Tricia Naicker^†, and Per I. Arvidsson^*‡

^† Catalysis and Peptide Research Unit, University of KwaZulu-Natal, Durban, 4041, South Africa

^‡ Science for Life Laboratory, Drug Discovery & Development Platform & Division of Translational Medicine and Chemical Biology, Department of Medical Biochemistry and Biophysics, Karolinska Institutet, SE-171 21 Stockholm, Sweden

J. Org. Chem., 2016, 81 (6), pp 2618–2623

DOI: 10.1021/acs.joc.5b02770

*E-mail: per.arvidsson@scilifelab.se.

 http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b02770




 GC MS

 HR MS

 

 

 

 

 
 Praveen Kumar

PhD

PostDoc Position

University of KwaZulu-Natal, Durban · School of Pharmacy and Pharmacology

• 
  University of KwaZulu-Natal

  School of Pharmacy and Pharmacology

  Durban, KwaZulu-Natal, South Africa

Research experience

• May 2014–
  present

  PostDoc Position

  University of KwaZulu-Natal · School of Pharmacy and Pharmacology · Catalysis and Peptide Research Unit
  South Africa · Durabn
• Jan 2009–
  Jan 2014

  SRF

  Indian Institute of Integrative Medicine · Bio-Organic Chemistry Division (IIIM) · Dr. S. Koul
  India · Jammu

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• Supporting Info 

 Douala, Cameroon.

Douala

City in Cameroon

Douala is the largest city in Cameroon, the capital of Cameroon's Littoral Region and the richest city in the whole CEMAC region of six countries. Wikipedia

 

 

 

 
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