One-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols

[Display omitted] •One-pot reaction.•Preparation of Julia-Kocienski sulfides from alcohols.•Preparation of Julia-Kocienski sulfones from alcohols.•Useful for alkene synthesis. A method for one-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols and thiols is reported. A variety of...

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Published in:Tetrahedron letters 2019-09, Vol.60 (36), p.151017, Article 151017
Main Authors: Ando, Kaori, Hattori, Junichiro
Format: Article
Language:English
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Julia-Kocienski reagents
One-pot reaction
Sulfides from alcohols
Sulfones from alcohols
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Hattori, Junichiro
description [Display omitted] •One-pot reaction.•Preparation of Julia-Kocienski sulfides from alcohols.•Preparation of Julia-Kocienski sulfones from alcohols.•Useful for alkene synthesis. A method for one-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols and thiols is reported. A variety of primary alcohols were converted to the corresponding mesylates by methansulfonyl chloride and triethylamine in THF. After the reaction is complete, thiol (1 or 10) and either NaH or t-BuOK were added. The Julia-Kocienski sulfides 3, 9 and 11 were prepared by one-pot two steps procedure from alcohols in 76–96% yields (16 examples). Furthermore, after the sulfide formation, the reaction mixture was neutralized by p-toluenesulfonic acid and treated with H2O2 and ammonium molybdate in EtOH to give the Julia-Kocienski sulfones 4 in good yields except for trans-2-hexen-1-ol.
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Furthermore, after the sulfide formation, the reaction mixture was neutralized by p-toluenesulfonic acid and treated with H2O2 and ammonium molybdate in EtOH to give the Julia-Kocienski sulfones 4 in good yields except for trans-2-hexen-1-ol.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2019.151017</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Julia-Kocienski reagents ; One-pot reaction ; Sulfides from alcohols ; Sulfones from alcohols</subject><ispartof>Tetrahedron letters, 2019-09, Vol.60 (36), p.151017, Article 151017</ispartof><rights>2019 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c372t-f01ac38ab2ed6b6c56dac2e6b43a532b657e736e5817ff7cd035afaa84a2cb373</citedby><cites>FETCH-LOGICAL-c372t-f01ac38ab2ed6b6c56dac2e6b43a532b657e736e5817ff7cd035afaa84a2cb373</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Ando, Kaori</creatorcontrib><creatorcontrib>Hattori, Junichiro</creatorcontrib><title>One-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols</title><title>Tetrahedron letters</title><description>[Display omitted] •One-pot reaction.•Preparation of Julia-Kocienski sulfides from alcohols.•Preparation of Julia-Kocienski sulfones from alcohols.•Useful for alkene synthesis. 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A method for one-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols and thiols is reported. A variety of primary alcohols were converted to the corresponding mesylates by methansulfonyl chloride and triethylamine in THF. After the reaction is complete, thiol (1 or 10) and either NaH or t-BuOK were added. The Julia-Kocienski sulfides 3, 9 and 11 were prepared by one-pot two steps procedure from alcohols in 76–96% yields (16 examples). Furthermore, after the sulfide formation, the reaction mixture was neutralized by p-toluenesulfonic acid and treated with H2O2 and ammonium molybdate in EtOH to give the Julia-Kocienski sulfones 4 in good yields except for trans-2-hexen-1-ol.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2019.151017</doi></addata></record>
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subjects Julia-Kocienski reagents
One-pot reaction
Sulfides from alcohols
Sulfones from alcohols
title One-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols
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