Editing Thioester (section)

==Reactions==
Thioesters hydrolyze to thiols and the carboxylic acid:
:{{chem2|RC(O)SR'  +  H2O  ->  RCO2H  +  RSH}}
The carbonyl center in thioesters is more reactive toward amine than oxygen nucleophiles, giving [[amide]]s:
:[[File:FormationofAmides.png|class=skin-invert-image|500px|Formation of amides from thioesters]]
[[Image:NCL mechanism.pdf|thumb|class=skin-invert-image|300px|right|Thioesters are components of the [[native chemical ligation]] method for peptide synthesis.]]
This reaction is exploited in [[native chemical ligation]], a protocol for [[peptide synthesis]].<ref>{{Cite journal |last1=McGrath |first1=N. A. |last2=Raines |first2=R. T. |title=Chemoselectivity in chemical biology: Acyl transfer reactions with sulfur and selenium |journal=Acc. Chem. Res. |year=2011 |volume=44 |pmid=21639109 |pmc=3242736 |pages=752–761 |doi=10.1021/ar200081s |issue=9}}</ref>

In a related reaction, thioesters can be converted into esters.<ref>{{cite journal|journal=Organic Syntheses|volume=61|page=48|year=1983|title=Preparation of O-esters From The Corresponding Thiol Esters: Tert-butyl Cyclohexanecarboxylate|author=Wan Kit Chan|author2=S. Masamune|author3=Gary O. Spessard|doi=10.15227/orgsyn.061.0048}}</ref>  Thioacetate esters can also be cleaved with methanethiol in the presence of stoichiometric base, as illustrated in the preparation of pent-4-yne-1-thiol:<ref>{{cite journal|title=4-Pentyne-1-thiol|author=Matteo Minozzi |author2=Daniele Nanni |author3=Piero Spagnolo |year=2008|doi=10.1002/047084289X.rn00855|journal=EEROS|isbn=978-0-471-93623-7 }}</ref>
:{{chem2|H3C(CH2)3OMs + KSAc -> H3C(CH2)3SAc  + KOMs}}
:{{chem2|H3C(CH2)3SAc + HSMe -> H3C(CH2)3SH  + MeSAc}}

A reaction unique to thioesters is the [[Fukuyama coupling]], in which the thioester is coupled with an [[organozinc halide]] by a palladium catalyst to give a ketone.
:[[Image:FukuyamaCoupling.svg|class=skin-invert-image|Fukuyama coupling]]