Alternative pathways for heck intermediates: Palladium-catalyzed oxyarylation of homoallylic alcohols

Chen Zhu; J R Falck

doi:10.1002/anie.201101857

Alternative pathways for heck intermediates: Palladium-catalyzed oxyarylation of homoallylic alcohols

Chen Zhu, J R Falck

Biochemistry

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

40 Scopus citations

Abstract

The oxidative Heck arylation of homoallylic alcohols affords adducts in good yields and regioselectivities owing largely to coordination between the catalyst and hydroxy group (see scheme). Moreover, the Heck intermediate can be intercepted by an intramolecular palladium-catalyzed olefin oxyannulation, thus leading to a wide range of α-aryltetrahydrofurans, including highly functionalized scaffolds.

Original language	English (US)
Pages (from-to)	6626-6629
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	29
DOIs	https://doi.org/10.1002/anie.201101857
State	Published - Jul 11 2011

Keywords

cyclization
homogeneous catalysis
olefin functionalization
oxyarylation
palladium

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.201101857

Cite this

@article{5084c3b2c01d4ccfa79bc03b12cab8a9,

title = "Alternative pathways for heck intermediates: Palladium-catalyzed oxyarylation of homoallylic alcohols",

abstract = "The oxidative Heck arylation of homoallylic alcohols affords adducts in good yields and regioselectivities owing largely to coordination between the catalyst and hydroxy group (see scheme). Moreover, the Heck intermediate can be intercepted by an intramolecular palladium-catalyzed olefin oxyannulation, thus leading to a wide range of α-aryltetrahydrofurans, including highly functionalized scaffolds.",

keywords = "cyclization, homogeneous catalysis, olefin functionalization, oxyarylation, palladium",

author = "Chen Zhu and Falck, {J R}",

year = "2011",

month = jul,

day = "11",

doi = "10.1002/anie.201101857",

language = "English (US)",

volume = "50",

pages = "6626--6629",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "29",

}

TY - JOUR

T1 - Alternative pathways for heck intermediates

T2 - Palladium-catalyzed oxyarylation of homoallylic alcohols

AU - Zhu, Chen

AU - Falck, J R

PY - 2011/7/11

Y1 - 2011/7/11

N2 - The oxidative Heck arylation of homoallylic alcohols affords adducts in good yields and regioselectivities owing largely to coordination between the catalyst and hydroxy group (see scheme). Moreover, the Heck intermediate can be intercepted by an intramolecular palladium-catalyzed olefin oxyannulation, thus leading to a wide range of α-aryltetrahydrofurans, including highly functionalized scaffolds.

AB - The oxidative Heck arylation of homoallylic alcohols affords adducts in good yields and regioselectivities owing largely to coordination between the catalyst and hydroxy group (see scheme). Moreover, the Heck intermediate can be intercepted by an intramolecular palladium-catalyzed olefin oxyannulation, thus leading to a wide range of α-aryltetrahydrofurans, including highly functionalized scaffolds.

KW - cyclization

KW - homogeneous catalysis

KW - olefin functionalization

KW - oxyarylation

KW - palladium

UR - http://www.scopus.com/inward/record.url?scp=79959923779&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79959923779&partnerID=8YFLogxK

U2 - 10.1002/anie.201101857

DO - 10.1002/anie.201101857

M3 - Article

C2 - 21656881

AN - SCOPUS:79959923779

SN - 1433-7851

VL - 50

SP - 6626

EP - 6629

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 29

ER -

Alternative pathways for heck intermediates: Palladium-catalyzed oxyarylation of homoallylic alcohols

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this