Synthesis of 2,2c-6-trisubstituted and 2,2c-,6,6--tetrasubstituted diaryl sulfides and diaryl sulfones by copper-promoted coupling and/or ortholithiation

Jonathan Clayden; James Senior

doi:10.1055/s-0029-1217986

Synthesis of 2,2c-6-trisubstituted and 2,2c-,6,6--tetrasubstituted diaryl sulfides and diaryl sulfones by copper-promoted coupling and/or ortholithiation

Jonathan Clayden, James Senior

Research output: Contribution to journal › Article › peer-review

Abstract

Stoichiometric copper(I) iodide, in the presence of potassium carbonate and ethylene glycol, promotes the coupling of even highly sterically encumbered 2,6-disubstituted thiophenols and aryl iodides to form hindered diarylsulfides. Hindered diarylsulfones may be made in a complementary fashion by ortholithiation of the sulfone oxidation products of less hindered diarylsulfides.

Original language	English
Pages (from-to)	2769-2772
Number of pages	3
Journal	SYNLETT
Issue number	17
DOIs	https://doi.org/10.1055/s-0029-1217986
Publication status	Published - 2009

Keywords

Copper
Coupling
Lithiation
Sulfide
Sulfone
Ullmann

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10.1055/s-0029-1217986

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title = "Synthesis of 2,2c-6-trisubstituted and 2,2c-,6,6--tetrasubstituted diaryl sulfides and diaryl sulfones by copper-promoted coupling and/or ortholithiation",

abstract = "Stoichiometric copper(I) iodide, in the presence of potassium carbonate and ethylene glycol, promotes the coupling of even highly sterically encumbered 2,6-disubstituted thiophenols and aryl iodides to form hindered diarylsulfides. Hindered diarylsulfones may be made in a complementary fashion by ortholithiation of the sulfone oxidation products of less hindered diarylsulfides.",

keywords = "Copper, Coupling, Lithiation, Sulfide, Sulfone, Ullmann",

author = "Jonathan Clayden and James Senior",

year = "2009",

doi = "10.1055/s-0029-1217986",

language = "English",

pages = "2769--2772",

journal = "SYNLETT",

issn = "1437-2096",

publisher = "Georg Thieme Verlag",

number = "17",

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T1 - Synthesis of 2,2c-6-trisubstituted and 2,2c-,6,6--tetrasubstituted diaryl sulfides and diaryl sulfones by copper-promoted coupling and/or ortholithiation

AU - Clayden, Jonathan

AU - Senior, James

PY - 2009

Y1 - 2009

N2 - Stoichiometric copper(I) iodide, in the presence of potassium carbonate and ethylene glycol, promotes the coupling of even highly sterically encumbered 2,6-disubstituted thiophenols and aryl iodides to form hindered diarylsulfides. Hindered diarylsulfones may be made in a complementary fashion by ortholithiation of the sulfone oxidation products of less hindered diarylsulfides.

AB - Stoichiometric copper(I) iodide, in the presence of potassium carbonate and ethylene glycol, promotes the coupling of even highly sterically encumbered 2,6-disubstituted thiophenols and aryl iodides to form hindered diarylsulfides. Hindered diarylsulfones may be made in a complementary fashion by ortholithiation of the sulfone oxidation products of less hindered diarylsulfides.

KW - Copper

KW - Coupling

KW - Lithiation

KW - Sulfide

KW - Sulfone

KW - Ullmann

U2 - 10.1055/s-0029-1217986

DO - 10.1055/s-0029-1217986

M3 - Article

SN - 1437-2096

SP - 2769

EP - 2772

JO - SYNLETT

JF - SYNLETT

IS - 17

ER -

Synthesis of 2,2c-6-trisubstituted and 2,2c-,6,6--tetrasubstituted diaryl sulfides and diaryl sulfones by copper-promoted coupling and/or ortholithiation

Abstract

Keywords

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