Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis

Abstract

The merits of thiol-click chemistry and its potential for making new forays into chemical synthesis and materials applications are described. Since thiols react to high yields under benign conditions with a vast range of chemical species, their utility extends to a large number of applications in the chemical, biological, physical, materials and engineering fields. This critical review provides insight into emerging venues for application as well as new mechanistic understanding of this exceptional chemistry in its many forms (81 references).

Porous polymer particles—A comprehensive guide to synthesis, characterization, functionalization and applications

“…The addition of thiyl radicals to alkene or alkyne bonds (thiol-ene and thiol-yne reactions, respectively) has recently gained considerable interest as novel metal-free 'click' reactions among polymer scientists [228][229][230]. We recently exploited thiol-ene/yne chemistries for producing functional porous beads via microfluidics [10].…”

“…From the several proposed click type reactions in the literature [326][327], two of them received much attention within the polymer society: Cu(I) catalyzed azide-alkyne cycloaddition (CuAAC) [328][329][330][331][332] and the addition of a thiyl radical to olefins (thiol-ene and thiol-yne) [230,[333][334] (Scheme 2).…”

Synthesis and reactivity of 6-mercapto-6H-dibenzo[c,e][1,2]oxaphosphinine 6-sulfide

“…The thiol-ene click reaction has proven to be a versatile tool in organic synthesis. [12][13][14][15] In particular, such a strong nucleophilic character has been used in the thiol-Michael reaction which is exploited extensively in synthesis and polymer modification since it leads to thioesters in very high yields. 16,17 Hence, in order to verify the nucleophilicity of compound 4, it was reacted in the presence of two acrylates as shown in scheme 2.…”

The Lock is the Key: Development of Novel Drugs through Receptor Based Combinatorial Chemistry

“…As thioacids are nucleophilic, readily dimerize, and present storage and stability issues, their preparation and handling is therefore very demanding. 61 Namelikonda et al optimized the one-pot deprotection/amidation variant of sulfo-click reaction in the presence and absence of Bcl-X L starting from the 9-fluorenylmethyl (Fm)-protected thioesters and sulfonylazides. 52 Optimal deprotection of Fm thioesters TA1'-TA3' prepared from thioacid building blocks TA1-TA3 was achieved in one minute at room temperature with 3.5% 1,8-diazabicycloundec-7-ene (DBU)/DMF.…”