Effect of ether versus ester tethering on Heck cyclizations

Steven R. Woodcock; Bruce P. Branchaud

doi:10.1016/j.tetlet.2005.08.072

Effect of ether versus ester tethering on Heck cyclizations

Steven R. Woodcock
, Bruce P. Branchaud

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

10 Scopus citations

Abstract

Ether tethers allow Heck cyclizations to proceed in high yields. Ester tethers lead to low yields. Styrene trapping experiments indicate that ester reactions form viable organopalladium intermediates that cannot cyclize efficiently.

Original language	English (US)
Pages (from-to)	7213-7215
Number of pages	3
Journal	Tetrahedron Letters
Volume	46
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2005.08.072
State	Published - Oct 17 2005
Externally published	Yes

Funding

We thank the Department of Education GAANN P200A010222-03 and the University of Oregon, for support.

Funders	Funder number
Department of Arts Education and Physical Education	P200A010222-03
Oregon State University/Oregon Health and Science University

Keywords

Ester rotation barrier
Heck cyclization
Tethered cyclization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.08.072

Cite this

@article{9fb89ffccd174b32b58c288101153fdf,

title = "Effect of ether versus ester tethering on Heck cyclizations",

abstract = "Ether tethers allow Heck cyclizations to proceed in high yields. Ester tethers lead to low yields. Styrene trapping experiments indicate that ester reactions form viable organopalladium intermediates that cannot cyclize efficiently.",

keywords = "Ester rotation barrier, Heck cyclization, Tethered cyclization",

author = "Woodcock, \{Steven R.\} and Branchaud, \{Bruce P.\}",

note = "Funding Information: We thank the Department of Education GAANN P200A010222-03 and the University of Oregon, for support. ",

year = "2005",

month = oct,

day = "17",

doi = "10.1016/j.tetlet.2005.08.072",

language = "English (US)",

volume = "46",

pages = "7213--7215",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

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T1 - Effect of ether versus ester tethering on Heck cyclizations

AU - Woodcock, Steven R.

AU - Branchaud, Bruce P.

N1 - Funding Information: We thank the Department of Education GAANN P200A010222-03 and the University of Oregon, for support.

PY - 2005/10/17

Y1 - 2005/10/17

N2 - Ether tethers allow Heck cyclizations to proceed in high yields. Ester tethers lead to low yields. Styrene trapping experiments indicate that ester reactions form viable organopalladium intermediates that cannot cyclize efficiently.

AB - Ether tethers allow Heck cyclizations to proceed in high yields. Ester tethers lead to low yields. Styrene trapping experiments indicate that ester reactions form viable organopalladium intermediates that cannot cyclize efficiently.

KW - Ester rotation barrier

KW - Heck cyclization

KW - Tethered cyclization

UR - https://www.scopus.com/pages/publications/24944518460

UR - https://www.scopus.com/pages/publications/24944518460#tab=citedBy

U2 - 10.1016/j.tetlet.2005.08.072

DO - 10.1016/j.tetlet.2005.08.072

M3 - Article

AN - SCOPUS:24944518460

SN - 0040-4039

VL - 46

SP - 7213

EP - 7215

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

Effect of ether versus ester tethering on Heck cyclizations

Abstract

Funding

Keywords

ASJC Scopus subject areas

Access to Document

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