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

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

7 Citations (Scopus)

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	4
Journal	SYNLETT
Issue number	17
DOIs	https://doi.org/10.1055/s-0029-1217986
Publication status	Published - 24 Sept 2009

Keywords

Copper
Coupling
Lithiation
Sulfide
Sulfone
Ullmann

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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",

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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 - 2009/9/24

Y1 - 2009/9/24

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

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U2 - 10.1055/s-0029-1217986

DO - 10.1055/s-0029-1217986

M3 - Article (Academic Journal)

AN - SCOPUS:70449382837

SN - 0936-5214

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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