Deoxycyanation of Alkyl Alcohols DOI Creative Commons

Carla Hümpel,

Jingjia Chen,

William G. Lyon

et al.

Published: Aug. 23, 2024

Cyano groups represent an important class of functional motifs in medicinal chemistry given their synthetic versatility and capacity to engage essential interactions with biological targets. However, the synthesis sterically hindered alkyl nitriles using non-toxic reagents remains challenging. Traditional methods often rely on toxic cyanide sources suffer from limited substrate scope. Herein, we report a photoredox catalyzed, metal-free deoxycyanation alcohols that allows rapid access wide array 1º, 2º, 3º cyanides reagents.

Language: Английский

Direct C(sp3)-H functionalization with aryl and alkyl radicals as intermolecular hydrogen atom transfer (HAT) agents DOI
Jia‐Lin Tu, Binbin Huang

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Recent years have witnessed the emergence of direct intermolecular C(sp

Language: Английский

Citations

9

N-Heterocyclic Carbene-Catalyzed SuFEx Reactions of Fluoroalkylated Secondary Benzylic Alcohols DOI

Zhihang Wei,

Fang Zhang, Qichao Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

An N-heterocyclic carbene (NHC)-catalyzed SuFEx reaction of fluoroalkylated secondary benzylic alcohols with sulfonyl fluorides and fluorosulfates affords fluorinated sulfonates sulfates in high yields.

Language: Английский

Citations

0

Activation of Carboxylic Acids by using Sulfonyl Chloride Reagent: A Simple One Pot Conversion of Carboxylic Acids to Alcohols DOI

Ranjan Kumar Panigrahi,

Samaresh Jana

Organic Preparations and Procedures International, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 12

Published: April 18, 2025

Language: Английский

Citations

0

Benzene‐1,3‐disulfonyl fluoride and Benzene‐1,3,5‐trisulfonyl fluoride: Low‐Cost, Stable, and Selective Reagents for SuFEx‐Driven Deoxyazidation DOI
Dharmendra S. Vishwakarma, John E. Moses

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(21), P. 4470 - 4477

Published: July 23, 2024

The development of synthetic methods for the synthesis organic azides is highly important, given their critical role in advancing click chemistry over last twenty years. We report a reagent-economical, reliable, and scalable alkyl from primary secondary alcohols. This robust method capitalizes on synergistic interaction between Sulfur Fluoride Exchange (SuFEx) reagents-specifically, benzene-1,3-disulfonyl fluoride (BDSF) or benzene-1,3,5-trisulfonyl (BTSF)-and trimethylsilyl azide (TMSN3). offers procedural ease, accommodates wide array substrates, enables late-stage functionalization. Additionally, we demonstrate protocol's adaptability by validating straightforward one-pot deoxyazidation-CuAAC sequence drug discovery applications.

Language: Английский

Citations

2

The First Decade of SuFEx Chemistry: Advancements in SuFEx Polymerization, Non-Canonical SuFEx Reactions, and SuFEx Radiochemistry DOI

Min Pyeong Kim,

Manoj Kumar Sahoo, Joong‐Hyun Chun

et al.

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 7, 2024

Abstract This year marks the 10th anniversary of SuFEx chemistry, a field that has witnessed significant advancements over past decade. These include efficient synthetic strategies toward polymerization via approach leading to diverse polymers, alongside discovery new SuFExable hubs and coupling conditions. Non-canonical reactions, such as deoxyfluorination on-water have also emerged. Furthermore, there been substantial strides in radiosynthesis [18F] hubs. review provides an overview these developments, focusing on polymerization, non-canonical reaction, radiochemistry chemistry. 1 Introduction 2 Polymerization 3 Non-Canonical Reactions 4 Fluorine-18 Radiochemistry 5 Conclusions Outlook

Language: Английский

Citations

0

Deoxycyanation of Alkyl Alcohols DOI Creative Commons

Carla Hümpel,

Jingjia Chen,

William G. Lyon

et al.

Published: Aug. 23, 2024

Cyano groups represent an important class of functional motifs in medicinal chemistry given their synthetic versatility and capacity to engage essential interactions with biological targets. However, the synthesis sterically hindered alkyl nitriles using non-toxic reagents remains challenging. Traditional methods often rely on toxic cyanide sources suffer from limited substrate scope. Herein, we report a photoredox catalyzed, metal-free deoxycyanation alcohols that allows rapid access wide array 1º, 2º, 3º cyanides reagents.

Language: Английский

Citations

0