Deoxygenative nucleophilic difluoromethylselenylation of carboxylic acids and alcohols with BT-SeCF₂H

Abstract

The benzothiazolium salt BT-SeCF2H is introduced as an efficient nucleophilic reagent for transferring difluoromethylselenyl groups onto organic molecules. SeCF2H-Containing selenoesters could be prepared upon deoxygenative substitution of readily available carboxylic...

Visible-Light Photocatalytic Synthesis of Difluoromethylated Selenides from Selenosulfonates through a Radical Process

“…HRMS (EI-TOF) m/z: [M] + calcd for C 13 H 20 F 2 O 5 Se + ,374.0444;found,374.0441. (4S,5′R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,6a,8a,3,3′,4,4′,5,5′,6,6a,6b,6′,7,8,8a,8b,9,11a,12,12a,1':4,5]indeno[2,1-B]furan-10,2′pyran]-4-yl 4-((Difluoromethyl)selanyl) Butanoate (3m). According to the general procedure, the title compound was synthesized from 1m (0.20 mmol, 140.8 mg).…”

“…In 2018, Zhang’s group presented a transition metal-free synthesis of RSeCF 2 H from selenocyanates and TMSCF 2 H under mild conditions . By means of developing new reagents, including BnSeCF 2 H, ClSeCF 2 H, TsSeCF 2 H, and BT-SeCF 2 H, the direct introduction of SeCF 2 H group has shown wide applications in modifying the organic molecules, but a multistep synthesis was required and a key precursor, BnSeCF 2 H, was obtained in low yields (10–36%). In the past few years, bench-stable and easily accessible difluoromethyltriphenylphosphonium salts have emerged as attractive tools for difluoromethylation reactions .…”

Silver‐Catalyzed Nucleophilic Deoxydifluoromethylthiolation of Activated Aliphatic Alcohols with BT−SCF2H

“…In 2019, we introduced benzothiazolium salts as new nucleophilic reagents for installing valuable fluorine‐containing groups into organic molecules [12,13] . Initially, these reagents were employed in deoxygenative trifluoromethylthiolation and selenylation reactions of aliphatic alcohols [12,14] while subsequent work focused on the synthesis of (fluoroalkyl)thio‐ and selenoesters directly from widely available carboxylic acids [14b,15,16] . In addition to (trifluoromethyl)thiolation using BT−SCF 3 , in the latter project, (difluoromethyl)thioesters could be prepared employing 2‐((difluoromethyl)thio)‐3‐methylbenzo[ d ]thiazol‐3‐ium triflate (BT−SCF 2 H, Scheme 1c).…”