Editing Thioester (section)

==Synthesis==
One route to thioesters involves the reaction of an [[acid chloride]] with an [[alkali metal]] salt of a thiol:<ref name=PATAI/>
:{{chem2|RSNa + R'COCl -> R'COSR + NaCl}}
Another common route entails the displacement of [[halide]]s by the alkali metal salt of a [[thiocarboxylic acid]]. For example, thioacetate esters are commonly prepared by [[alkylation]] of [[potassium thioacetate]]:<ref name=PATAI/>
:{{chem2|CH3COSK + RX -> CH3COSR + KX}}
The analogous alkylation of an acetate salt is rarely practiced. The alkylation can be conducted using [[Mannich base]]s and the thiocarboxylic acid:
:{{chem2|CH3COSH + R'2NCH2OH -> CH3COSCH2NR'2 + H2O}}

Thioesters can be prepared by condensation of thiols and carboxylic acids in the presence of [[Desiccant|dehydrating agent]]s:<ref>{{cite book | last1 = Fujiwara | first1 = S. | last2 = Kambe | first2 = N. | chapter = Thio-, Seleno-, and Telluro-Carboxylic Acid Esters | title = Topics in Current Chemistry | year = 2005 | volume = 251 | pages = 87–140 | publisher = Springer | location = Berlin / Heidelberg | doi = 10.1007/b101007 | isbn = 978-3-540-23012-0 }}</ref><ref>{{cite web | url = https://www.organic-chemistry.org/synthesis/C1S/thioesters.shtm | title = Synthesis of thioesters | publisher = Organic Chemistry Portal }}</ref>
:{{chem2|RSH + R'CO2H -> RSC(O)R' + H2O}}
A typical dehydration agent is [[N,N'-Dicyclohexylcarbodiimide|DCC]].<ref>{{OrgSynth | last1 = Mori | first1 = Y. | last2 = Seki | first2 = M. | year = 2007 | title = Synthesis of Multifunctionalized Ketones Through the Fukuyama Coupling Reaction Catalyzed by Pearlman's Catalyst: Preparation of Ethyl 6-oxotridecanoate | volume = 84 | pages = 285 | collvol = 11 | collvolpages = 281 | prep = V84P0285 }}</ref> Efforts to improve the sustainability of thioester synthesis have also been reported utilising safer coupling reagent [[Propanephosphonic acid anhydride|T3P]] and greener solvent [[cyclopentanone]].<ref>{{cite journal |last1=Jordan |first1=Andrew |last2=Sneddon |first2=Helen F. |title=Development of a solvent-reagent selection guide for the formation of thioesters |journal=Green Chemistry |date=2019 |volume=21 |issue=8 |pages=1900–1906 |doi=10.1039/C9GC00355J|s2cid=107391323 }}</ref> [[Acid anhydride]]s and some [[lactone]]s also give thioesters upon treatment with thiols in the presence of a base.

Thioesters can be conveniently prepared from alcohols by the [[Mitsunobu reaction]], using [[thioacetic acid]].<ref>{{cite journal | last = Volante | first = R. | title = A new, highly efficient method for the conversion of alcohols to thiolesters and thiols | journal = [[Tetrahedron Letters]] | year = 1981 | volume = 22 | issue = 33 | pages = 3119–3122 | doi = 10.1016/S0040-4039(01)81842-6}}</ref>

They also arise via [[carbonylation]] of [[alkyne]]s and [[alkene]]s in the presence of thiols.<ref>{{ Ullmann | author = Bertleff, W. | author2 = Roeper, M. | author3 = Sava, X. | title = Carbonylation | doi = 10.1002/14356007.a05_217.pub2}}</ref>