Synthesis 2023; 55(05): 837-845
DOI: 10.1055/a-1961-8013
paper

Development, Synthesis, and in silico Investigations of Novel Acyclic Allyl Fluoride Derivatives

Nishita Chauhan
a   Department of Chemistry & Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh 160014, India
,
Harjinder Singh
b   P. G. Department of Chemistry, Multani Mal Modi College, Patiala, Punjab 147001, India
,
Kamal Nain Singh
a   Department of Chemistry & Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh 160014, India
,
Jeffrey M. McKenna
c   Novartis Institutes of BioMedical Research, Lichtstrasse 35, Basel 4056, Switzerland
,
Vaneet Saini
a   Department of Chemistry & Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh 160014, India
› Author Affiliations
V.S. thanks Department of Science and Technology for DST-Inspire Faculty grant (DST/INSPIRE/04/2017/002529).


Abstract

A one step electrophilic fluorination of alkenes is reported, which furnishes the products in a highly regioselective manner via allylic rearrangement. The reaction proceeds efficiently under mild conditions with the use of trisubstituted alkenes as olefin partner and Selectfluor as an electrophilic fluorinating agent without the need of any transition metal catalyst or pre-functionalized substrates. Virtual screening of the newly synthesized compounds shows their potential application as herbicides by inhibiting protoporphyrinogen oxidase (PPO) enzyme.

Supporting Information



Publication History

Received: 24 June 2022

Accepted after revision: 17 October 2022

Accepted Manuscript online:
17 October 2022

Article published online:
23 November 2022

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