Catalytic carbonylation of 4-penten-1-ol to ε-caprolactone and oligocaprolactone

Jeffrey K. Funk; David K. Newsham; David N. Goldstein; Shengsheng Liu; Ayusman Sen

doi:10.1016/j.molcata.2005.06.013

Catalytic carbonylation of 4-penten-1-ol to ε-caprolactone and oligocaprolactone

Jeffrey K. Funk
, David K. Newsham
, David N. Goldstein
, Shengsheng Liu
, Ayusman Sen

Chemistry

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

4 Scopus citations

Abstract

A catalyst consisting of Pd₂(dba)₃ + 2 XANTPhos (dba = dibenzylideneacetone, XANTPhos = 9,9-dimethyl-4,5-bis(diphenylphosphino) xanthene) in toluene catalyzes the alkoxycarbonylation of 4-penten-1-ol to form the cyclic products ε-caprolactone and 2-methylvalerolactone, as well as oligocaprolactone. The conversion and selectivity observed using this catalyst is higher than that observed with other reported systems with the regioselectivity for terminal carbonylation exceeding 70%.

Original language	English (US)
Pages (from-to)	185-192
Number of pages	8
Journal	Journal of Molecular Catalysis A: Chemical
Volume	239
Issue number	1-2
DOIs	https://doi.org/10.1016/j.molcata.2005.06.013
State	Published - Sep 14 2005

All Science Journal Classification (ASJC) codes

Catalysis
Process Chemistry and Technology
Physical and Theoretical Chemistry

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10.1016/j.molcata.2005.06.013

Cite this

@article{9f8044bcf4ce4c688fe6fb42b572fb2e,

title = "Catalytic carbonylation of 4-penten-1-ol to ε-caprolactone and oligocaprolactone",

abstract = "A catalyst consisting of Pd2(dba)3 + 2 XANTPhos (dba = dibenzylideneacetone, XANTPhos = 9,9-dimethyl-4,5-bis(diphenylphosphino) xanthene) in toluene catalyzes the alkoxycarbonylation of 4-penten-1-ol to form the cyclic products ε-caprolactone and 2-methylvalerolactone, as well as oligocaprolactone. The conversion and selectivity observed using this catalyst is higher than that observed with other reported systems with the regioselectivity for terminal carbonylation exceeding 70\%.",

author = "Funk, \{Jeffrey K.\} and Newsham, \{David K.\} and Goldstein, \{David N.\} and Shengsheng Liu and Ayusman Sen",

note = "Funding Information: We thank the U.S. Department of Energy, Office of Basic Energy Sciences for financial support. ",

year = "2005",

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doi = "10.1016/j.molcata.2005.06.013",

language = "English (US)",

volume = "239",

pages = "185--192",

journal = "Journal of Molecular Catalysis A: Chemical",

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TY - JOUR

T1 - Catalytic carbonylation of 4-penten-1-ol to ε-caprolactone and oligocaprolactone

AU - Funk, Jeffrey K.

AU - Newsham, David K.

AU - Goldstein, David N.

AU - Liu, Shengsheng

AU - Sen, Ayusman

N1 - Funding Information: We thank the U.S. Department of Energy, Office of Basic Energy Sciences for financial support.

PY - 2005/9/14

Y1 - 2005/9/14

N2 - A catalyst consisting of Pd2(dba)3 + 2 XANTPhos (dba = dibenzylideneacetone, XANTPhos = 9,9-dimethyl-4,5-bis(diphenylphosphino) xanthene) in toluene catalyzes the alkoxycarbonylation of 4-penten-1-ol to form the cyclic products ε-caprolactone and 2-methylvalerolactone, as well as oligocaprolactone. The conversion and selectivity observed using this catalyst is higher than that observed with other reported systems with the regioselectivity for terminal carbonylation exceeding 70%.

AB - A catalyst consisting of Pd2(dba)3 + 2 XANTPhos (dba = dibenzylideneacetone, XANTPhos = 9,9-dimethyl-4,5-bis(diphenylphosphino) xanthene) in toluene catalyzes the alkoxycarbonylation of 4-penten-1-ol to form the cyclic products ε-caprolactone and 2-methylvalerolactone, as well as oligocaprolactone. The conversion and selectivity observed using this catalyst is higher than that observed with other reported systems with the regioselectivity for terminal carbonylation exceeding 70%.

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DO - 10.1016/j.molcata.2005.06.013

M3 - Article

AN - SCOPUS:23344451600

SN - 1381-1169

VL - 239

SP - 185

EP - 192

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

IS - 1-2

ER -

Catalytic carbonylation of 4-penten-1-ol to ε-caprolactone and oligocaprolactone

Abstract

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