Smedley, Christopher J, Homer, Joshua A, Gialelis, Timothy L, Barrow, Andrew S, Koelln, Rebecca A, Moses, John Edward (November 2021) Accelerated SuFEx Click Chemistry For Modular Synthesis. Angewandte Chemie International Edition. ISSN 1433-7851
Abstract
SuFEx click chemistry is a powerful method designed for the selective, rapid and modular synthesis of functional molecules. Classical SuFEx reactions form stable S-O linkages upon exchange of S-F bonds with aryl silyl-ether substrates, and while near-perfect in their outcome, are sometimes disadvantaged by relatively high catalyst loadings and prolonged reaction times. We herein report the development of 'Accelerated SuFEx Click Chemistry' (ASCC), an improved SuFEx method for the efficient and catalytic coupling of aryl and alkyl alcohols with a range of SuFExable hubs. We demonstrate Barton's hindered guanidine base (2- tert -butyl-1,1,3,3-tetramethylguanidine; BTMG) as a superb SuFEx catalyst that, when used in synergy with silicon additive hexamethyldisilazane (HMDS), yields stable S-O bond linkages in a single step; often within minutes. The powerful combination of BTMG and HMDS reagents allows for catalyst loadings as low as 1.0 mol% and, in congruence with click-principles, provides a scalable method that is safe, efficient, and practical for modular synthesis. ASSC expands the number of accessible SuFEx products and will find significant application in organic synthesis, medicinal chemistry, chemical biology, and materials science .
| Item Type: | Paper |
|---|---|
| Subjects: | chemistry > techniques > click chemistry > Accelerated SuFEx Click Chemistry chemistry > chemicals chemistry > techniques > click chemistry chemistry > chemicals > guanidines |
| CSHL Authors: | |
| Communities: | CSHL labs > Moses lab CSHL Cancer Center Program CSHL Cancer Center Program > Gene Regulation and Inheritance Program |
| SWORD Depositor: | CSHL Elements |
| Depositing User: | CSHL Elements |
| Date: | 9 November 2021 |
| Date Deposited: | 17 Nov 2021 16:38 |
| Last Modified: | 09 Feb 2024 20:25 |
| PMCID: | PMC8867595 |
| URI: | https://repository.cshl.edu/id/eprint/40426 |
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