Issue 11, 2021

Hexafluoroisopropanol: the magical solvent for Pd-catalyzed C–H activation

Abstract

Among numerous solvents available for chemical transformations, 1,1,1,3,3,3-hexafluoro-2-propanol (popularly known as HFIP) has attracted enough attention of the scientific community in recent years. Several unique features of HFIP compared to its non-fluoro analogue isopropanol have helped this solvent to make a difference in various subdomains of organic chemistry. One such area is transition metal-catalyzed C–H bond functionalization reactions. While, on one side, HFIP is emerging as a green and sustainable deep eutectic solvent (DES), on the other side, a major proportion of Pd-catalyzed C–H functionalization is heavily relying on this solvent. In particular, for distal aromatic C–H functionalizations, the exceptional impact of HFIP to elevate the yield and selectivity has made this solvent irreplaceable. Recent research studies have also highlighted the H-bond-donating ability of HFIP to enhance the chiral induction in Pd-catalyzed atroposelective C–H activation. This perspective aims to portray different shades of HFIP as a magical solvent in Pd-catalyzed C–H functionalization reactions.

Graphical abstract: Hexafluoroisopropanol: the magical solvent for Pd-catalyzed C–H activation

Article information

Article type
Review Article
Submitted
21 12 2020
Accepted
19 1 2021
First published
10 2 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 3857-3870

Hexafluoroisopropanol: the magical solvent for Pd-catalyzed C–H activation

T. Bhattacharya, A. Ghosh and D. Maiti, Chem. Sci., 2021, 12, 3857 DOI: 10.1039/D0SC06937J

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