Catalytic Dimerization of Crotonates

James C.A. Flanagan; Eun Joo Kang; Nathaniel I. Strong; Robert M. Waymouth

doi:10.1021/acscatal.5b00930

Catalytic Dimerization of Crotonates

James C.A. Flanagan
, Eun Joo Kang
, Nathaniel I. Strong
, Robert M. Waymouth

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

27 Citations (Scopus)

Abstract

A room-temperature dimerization of crotonates into 2-ethylidene-3-methylpentanedioates provides a sustainable route to difunctional monomers for step-growth polymerizations. We report two such dimerizations: (1) an organocatalytic dimerization using the N-heterocyclic carbene 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (IⁱPr₂Me₂) and (2) a rapid dimerization (under 15 s to full conversion) using potassium t-butoxide in THF. In addition to unsaturated diesters, the resulting dimers can be easily converted to other step-growth monomers; namely, their corresponding diacids and saturated diesters.

Original language	English
Pages (from-to)	5328-5332
Number of pages	5
Journal	ACS Catalysis
Volume	5
Issue number	9
DOIs	https://doi.org/10.1021/acscatal.5b00930
Publication status	Published - 10 Aug 2015

Bibliographical note

Publisher Copyright:
© 2015 American Chemical Society.

Keywords

N-heterocyclic carbenes
alkenoates
base catalysis
dimerization
monomer synthesis

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10.1021/acscatal.5b00930

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title = "Catalytic Dimerization of Crotonates",

abstract = "A room-temperature dimerization of crotonates into 2-ethylidene-3-methylpentanedioates provides a sustainable route to difunctional monomers for step-growth polymerizations. We report two such dimerizations: (1) an organocatalytic dimerization using the N-heterocyclic carbene 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (IiPr2Me2) and (2) a rapid dimerization (under 15 s to full conversion) using potassium t-butoxide in THF. In addition to unsaturated diesters, the resulting dimers can be easily converted to other step-growth monomers; namely, their corresponding diacids and saturated diesters.",

keywords = "N-heterocyclic carbenes, alkenoates, base catalysis, dimerization, monomer synthesis",

author = "Flanagan, \{James C.A.\} and Kang, \{Eun Joo\} and Strong, \{Nathaniel I.\} and Waymouth, \{Robert M.\}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

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doi = "10.1021/acscatal.5b00930",

language = "English",

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TY - JOUR

T1 - Catalytic Dimerization of Crotonates

AU - Flanagan, James C.A.

AU - Kang, Eun Joo

AU - Strong, Nathaniel I.

AU - Waymouth, Robert M.

PY - 2015/8/10

Y1 - 2015/8/10

N2 - A room-temperature dimerization of crotonates into 2-ethylidene-3-methylpentanedioates provides a sustainable route to difunctional monomers for step-growth polymerizations. We report two such dimerizations: (1) an organocatalytic dimerization using the N-heterocyclic carbene 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (IiPr2Me2) and (2) a rapid dimerization (under 15 s to full conversion) using potassium t-butoxide in THF. In addition to unsaturated diesters, the resulting dimers can be easily converted to other step-growth monomers; namely, their corresponding diacids and saturated diesters.

AB - A room-temperature dimerization of crotonates into 2-ethylidene-3-methylpentanedioates provides a sustainable route to difunctional monomers for step-growth polymerizations. We report two such dimerizations: (1) an organocatalytic dimerization using the N-heterocyclic carbene 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (IiPr2Me2) and (2) a rapid dimerization (under 15 s to full conversion) using potassium t-butoxide in THF. In addition to unsaturated diesters, the resulting dimers can be easily converted to other step-growth monomers; namely, their corresponding diacids and saturated diesters.

KW - N-heterocyclic carbenes

KW - alkenoates

KW - base catalysis

KW - dimerization

KW - monomer synthesis

UR - https://www.scopus.com/pages/publications/84941054272

U2 - 10.1021/acscatal.5b00930

DO - 10.1021/acscatal.5b00930

M3 - Article

AN - SCOPUS:84941054272

SN - 2155-5435

VL - 5

SP - 5328

EP - 5332

JO - ACS Catalysis

JF - ACS Catalysis

IS - 9

ER -

Catalytic Dimerization of Crotonates

Abstract

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