Pd(DPEPhos)Cl2-catalyzed Negishi cross-couplings for the formation of biaryl and diarylmethane phloroglucinol adducts

Eric Dennis; David Jeffery; Michael Perkins; Paul Smith

doi:10.1016/j.tet.2011.01.030

Pd(DPEPhos)Cl2-catalyzed Negishi cross-couplings for the formation of biaryl and diarylmethane phloroglucinol adducts

Eric Dennis, David Jeffery, Michael Perkins, Paul Smith

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

14 Citations (Scopus)

Abstract

Several functionalized biaryls and diarylmethanes containing the phloroglucinol subunit were synthesized in 55-85% yields using Negishi cross-couplings of 2,4,6-trimethoxyphenylzinc chloride with aryl and benzyl halides in the presence of catalytic quantities of Pd(DPEPhos)Cl₂. These simple to prepare couplings were generally complete in 1-24 h depending on the halide, and were applicable to aryl and benzyl halides containing both electron-donating and electron-withdrawing groups.

Original language	English
Pages (from-to)	2125-2131
Number of pages	7
Journal	Tetrahedron
Volume	67
Issue number	11
DOIs	https://doi.org/10.1016/j.tet.2011.01.030
Publication status	Published - 18 Mar 2011

Keywords

Biaryls
Catechin
Diarylmethanes
Negishi cross-coupling
Organozinc
Phloroglucinol

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10.1016/j.tet.2011.01.030

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title = "Pd(DPEPhos)Cl2-catalyzed Negishi cross-couplings for the formation of biaryl and diarylmethane phloroglucinol adducts",

abstract = "Several functionalized biaryls and diarylmethanes containing the phloroglucinol subunit were synthesized in 55-85% yields using Negishi cross-couplings of 2,4,6-trimethoxyphenylzinc chloride with aryl and benzyl halides in the presence of catalytic quantities of Pd(DPEPhos)Cl2. These simple to prepare couplings were generally complete in 1-24 h depending on the halide, and were applicable to aryl and benzyl halides containing both electron-donating and electron-withdrawing groups.",

keywords = "Biaryls, Catechin, Diarylmethanes, Negishi cross-coupling, Organozinc, Phloroglucinol",

author = "Eric Dennis and David Jeffery and Michael Perkins and Paul Smith",

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T1 - Pd(DPEPhos)Cl2-catalyzed Negishi cross-couplings for the formation of biaryl and diarylmethane phloroglucinol adducts

AU - Dennis, Eric

AU - Jeffery, David

AU - Perkins, Michael

AU - Smith, Paul

PY - 2011/3/18

Y1 - 2011/3/18

N2 - Several functionalized biaryls and diarylmethanes containing the phloroglucinol subunit were synthesized in 55-85% yields using Negishi cross-couplings of 2,4,6-trimethoxyphenylzinc chloride with aryl and benzyl halides in the presence of catalytic quantities of Pd(DPEPhos)Cl2. These simple to prepare couplings were generally complete in 1-24 h depending on the halide, and were applicable to aryl and benzyl halides containing both electron-donating and electron-withdrawing groups.

AB - Several functionalized biaryls and diarylmethanes containing the phloroglucinol subunit were synthesized in 55-85% yields using Negishi cross-couplings of 2,4,6-trimethoxyphenylzinc chloride with aryl and benzyl halides in the presence of catalytic quantities of Pd(DPEPhos)Cl2. These simple to prepare couplings were generally complete in 1-24 h depending on the halide, and were applicable to aryl and benzyl halides containing both electron-donating and electron-withdrawing groups.

KW - Biaryls

KW - Catechin

KW - Diarylmethanes

KW - Negishi cross-coupling

KW - Organozinc

KW - Phloroglucinol

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DO - 10.1016/j.tet.2011.01.030

M3 - Article

SN - 0040-4020

VL - 67

SP - 2125

EP - 2131

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -

Pd(DPEPhos)Cl2-catalyzed Negishi cross-couplings for the formation of biaryl and diarylmethane phloroglucinol adducts

Abstract

Keywords

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