Sulfur Fluoride Exchange (SuFEx)

M. C. Giel; C. J. Smedley; J. E. Moses

doi:10.1055/sos-SD-235-00230

Sulfur Fluoride Exchange (SuFEx)

M. C. Giel, C. J. Smedley, J. E. Moses

Medicinal Chemistry

Research output: Chapter in Book/Report/Conference proceeding › Chapter (Book) › Other › peer-review

6 Citations (Scopus)

Abstract

Sulfur Fluoride Exchange (SuFEx) click chemistry is a new generation technology for creating stable molecular connections with absolute reliability under metal-free conditions. SuFEx builds upon the fundamental principles of click chemistry by exploiting a unique blend of stability and latent reactivity of high oxidation state sulfur fluoride [e.g., S(VI)] functionalities to forge stable covalent linkages at connective SuFEx hubs. In this review, we focus mainly on the SuFEx hubs, sulfuryl fluoride (SO₂F₂), thionyl tetrafluoride (SOF₄), ethenesulfonyl fluoride (ESF), 1-bromoethene-1-sulfonyl fluoride (BESF) and, 2-substituted alkyne-1-sulfonyl fluorides (SASFs). We describe each connector's unique reactivity and their application to SuFEx click chemistry.

Original language	English
Title of host publication	Click Chemistry
Editors	Floris P J T Rutjes
Place of Publication	Stuttgart Germany
Publisher	Georg Thieme
Chapter	5
Pages	435-484
Number of pages	50
Edition	1st
ISBN (Electronic)	9783132435575
ISBN (Print)	9783132435568
DOIs	https://doi.org/10.1055/sos-SD-235-00230
Publication status	Published - 2022

Publication series

Name	Science of Synthesis
Number	4
Volume	2021
ISSN (Print)	2510-5469
ISSN (Electronic)	2566-7297

Keywords

1-bromoethene-1-sulfonyl fluoride
2-substituted alkyne-1-sulfonyl fluorides
click chemistry
connective hubs
diversity-oriented click reactions
ethenesulfonyl fluoride
sulfur fluoride exchange (SuFEx)
sulfur fluorides
sulfuryl fluoride
thionyl tetrafluoride

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10.1055/sos-SD-235-00230

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abstract = "Sulfur Fluoride Exchange (SuFEx) click chemistry is a new generation technology for creating stable molecular connections with absolute reliability under metal-free conditions. SuFEx builds upon the fundamental principles of click chemistry by exploiting a unique blend of stability and latent reactivity of high oxidation state sulfur fluoride [e.g., S(VI)] functionalities to forge stable covalent linkages at connective SuFEx hubs. In this review, we focus mainly on the SuFEx hubs, sulfuryl fluoride (SO2F2), thionyl tetrafluoride (SOF4), ethenesulfonyl fluoride (ESF), 1-bromoethene-1-sulfonyl fluoride (BESF) and, 2-substituted alkyne-1-sulfonyl fluorides (SASFs). We describe each connector's unique reactivity and their application to SuFEx click chemistry.",

keywords = "1-bromoethene-1-sulfonyl fluoride, 2-substituted alkyne-1-sulfonyl fluorides, click chemistry, connective hubs, diversity-oriented click reactions, ethenesulfonyl fluoride, sulfur fluoride exchange (SuFEx), sulfur fluorides, sulfuryl fluoride, thionyl tetrafluoride",

author = "Giel, \{M. C.\} and Smedley, \{C. J.\} and Moses, \{J. E.\}",

year = "2022",

doi = "10.1055/sos-SD-235-00230",

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AU - Giel, M. C.

AU - Smedley, C. J.

AU - Moses, J. E.

PY - 2022

Y1 - 2022

N2 - Sulfur Fluoride Exchange (SuFEx) click chemistry is a new generation technology for creating stable molecular connections with absolute reliability under metal-free conditions. SuFEx builds upon the fundamental principles of click chemistry by exploiting a unique blend of stability and latent reactivity of high oxidation state sulfur fluoride [e.g., S(VI)] functionalities to forge stable covalent linkages at connective SuFEx hubs. In this review, we focus mainly on the SuFEx hubs, sulfuryl fluoride (SO2F2), thionyl tetrafluoride (SOF4), ethenesulfonyl fluoride (ESF), 1-bromoethene-1-sulfonyl fluoride (BESF) and, 2-substituted alkyne-1-sulfonyl fluorides (SASFs). We describe each connector's unique reactivity and their application to SuFEx click chemistry.

AB - Sulfur Fluoride Exchange (SuFEx) click chemistry is a new generation technology for creating stable molecular connections with absolute reliability under metal-free conditions. SuFEx builds upon the fundamental principles of click chemistry by exploiting a unique blend of stability and latent reactivity of high oxidation state sulfur fluoride [e.g., S(VI)] functionalities to forge stable covalent linkages at connective SuFEx hubs. In this review, we focus mainly on the SuFEx hubs, sulfuryl fluoride (SO2F2), thionyl tetrafluoride (SOF4), ethenesulfonyl fluoride (ESF), 1-bromoethene-1-sulfonyl fluoride (BESF) and, 2-substituted alkyne-1-sulfonyl fluorides (SASFs). We describe each connector's unique reactivity and their application to SuFEx click chemistry.

KW - 1-bromoethene-1-sulfonyl fluoride

KW - 2-substituted alkyne-1-sulfonyl fluorides

KW - click chemistry

KW - connective hubs

KW - diversity-oriented click reactions

KW - ethenesulfonyl fluoride

KW - sulfur fluoride exchange (SuFEx)

KW - sulfur fluorides

KW - sulfuryl fluoride

KW - thionyl tetrafluoride

UR - https://www.scopus.com/pages/publications/85202884074

U2 - 10.1055/sos-SD-235-00230

DO - 10.1055/sos-SD-235-00230

M3 - Chapter (Book)

AN - SCOPUS:85202884074

SN - 9783132435568

T3 - Science of Synthesis

SP - 435

EP - 484

BT - Click Chemistry

A2 - Rutjes, Floris P J T

PB - Georg Thieme

CY - Stuttgart Germany

ER -

Sulfur Fluoride Exchange (SuFEx)

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Keywords

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