Highly regio- and chemoselective palladium(0)-mediated allylic substitution of difunctional allylic halides with phenols

Anant R. Kapdi; Richard J. K. Taylor; Ian J. S. Fairlamb

doi:10.1016/j.tetlet.2010.09.125

Highly regio- and chemoselective palladium(0)-mediated allylic substitution of difunctional allylic halides with phenols

Anant R. Kapdi, Richard J. K. Taylor, Ian J. S. Fairlamb

Chemistry

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

Abstract

An efficient Pd(0)-mediated, base-assisted reaction of phenols with difunctionalised allylic halides results in the formation of coupled products in good yields. The reactions proceed with excellent stereo-, regio- and chemocontrol. An appropriately functionalised Weinreb amide, synthesised by this methodology, undergoes halogen-lithium exchange and subsequent intramolecular 1,2-carbonyl addition/elimination to give an advanced macrocyclic intermediate with potential use in the synthesis of likonide B. (C) 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6378-6380
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	49
DOIs	https://doi.org/10.1016/j.tetlet.2010.09.125
Publication status	Published - 8 Dec 2010

Keywords

Pd(0)-mediated reactions
Allylic substitution
Bifunctional allylic halides
Regioselective
Chemoselective
LIKONIDE-B
CATALYZED 1,4-DIACETOXYLATION
PROTEIN PRENYLATION
FARNESOL ANALOGS
THP ETHERS
LIGAND
(+/-)-SMENOCHROMENE-D
TRANSFERASE
METHYLATION
DIPHOSPHATE

Access to Document

10.1016/j.tetlet.2010.09.125

Cite this

@article{59808be62c7a4052bdefc0cbd7241058,

title = "Highly regio- and chemoselective palladium(0)-mediated allylic substitution of difunctional allylic halides with phenols",

abstract = "An efficient Pd(0)-mediated, base-assisted reaction of phenols with difunctionalised allylic halides results in the formation of coupled products in good yields. The reactions proceed with excellent stereo-, regio- and chemocontrol. An appropriately functionalised Weinreb amide, synthesised by this methodology, undergoes halogen-lithium exchange and subsequent intramolecular 1,2-carbonyl addition/elimination to give an advanced macrocyclic intermediate with potential use in the synthesis of likonide B. (C) 2010 Elsevier Ltd. All rights reserved.",

keywords = "Pd(0)-mediated reactions, Allylic substitution, Bifunctional allylic halides, Regioselective, Chemoselective, LIKONIDE-B, CATALYZED 1,4-DIACETOXYLATION, PROTEIN PRENYLATION, FARNESOL ANALOGS, THP ETHERS, LIGAND, (+/-)-SMENOCHROMENE-D, TRANSFERASE, METHYLATION, DIPHOSPHATE",

author = "Kapdi, {Anant R.} and Taylor, {Richard J. K.} and Fairlamb, {Ian J. S.}",

year = "2010",

month = dec,

day = "8",

doi = "10.1016/j.tetlet.2010.09.125",

language = "English",

volume = "51",

pages = "6378--6380",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "49",

}

TY - JOUR

T1 - Highly regio- and chemoselective palladium(0)-mediated allylic substitution of difunctional allylic halides with phenols

AU - Kapdi, Anant R.

AU - Taylor, Richard J. K.

AU - Fairlamb, Ian J. S.

PY - 2010/12/8

Y1 - 2010/12/8

N2 - An efficient Pd(0)-mediated, base-assisted reaction of phenols with difunctionalised allylic halides results in the formation of coupled products in good yields. The reactions proceed with excellent stereo-, regio- and chemocontrol. An appropriately functionalised Weinreb amide, synthesised by this methodology, undergoes halogen-lithium exchange and subsequent intramolecular 1,2-carbonyl addition/elimination to give an advanced macrocyclic intermediate with potential use in the synthesis of likonide B. (C) 2010 Elsevier Ltd. All rights reserved.

AB - An efficient Pd(0)-mediated, base-assisted reaction of phenols with difunctionalised allylic halides results in the formation of coupled products in good yields. The reactions proceed with excellent stereo-, regio- and chemocontrol. An appropriately functionalised Weinreb amide, synthesised by this methodology, undergoes halogen-lithium exchange and subsequent intramolecular 1,2-carbonyl addition/elimination to give an advanced macrocyclic intermediate with potential use in the synthesis of likonide B. (C) 2010 Elsevier Ltd. All rights reserved.

KW - Pd(0)-mediated reactions

KW - Allylic substitution

KW - Bifunctional allylic halides

KW - Regioselective

KW - Chemoselective

KW - LIKONIDE-B

KW - CATALYZED 1,4-DIACETOXYLATION

KW - PROTEIN PRENYLATION

KW - FARNESOL ANALOGS

KW - THP ETHERS

KW - LIGAND

KW - (+/-)-SMENOCHROMENE-D

KW - TRANSFERASE

KW - METHYLATION

KW - DIPHOSPHATE

UR - http://www.scopus.com/inward/record.url?scp=78149280635&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.09.125

DO - 10.1016/j.tetlet.2010.09.125

M3 - Article

SN - 0040-4039

VL - 51

SP - 6378

EP - 6380

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 49

ER -

Highly regio- and chemoselective palladium(0)-mediated allylic substitution of difunctional allylic halides with phenols

Abstract

Keywords

Access to Document

Other files and links

Cite this