Group VIII carbamoyl complexes as catalysts for alkyne hydrocarboxylation and electrochemical proton reduction

Chandan Kr Barik; Malcolm E. Tessensohn; Richard D. Webster; Weng Kee Leong

doi:10.1016/j.jorganchem.2019.03.019

Group VIII carbamoyl complexes as catalysts for alkyne hydrocarboxylation and electrochemical proton reduction

Chandan Kr Barik, Malcolm E. Tessensohn, Richard D. Webster, Weng Kee Leong^*

^*Corresponding author for this work

Nanyang Technological University

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

8 Citations (Scopus)

Abstract

A series of group VIII carbamoyl complexes, [M(2-NHC(O)C₅H₄N)(CO)₂(2-SC₅H₄N)] [where M = Fe, Ru and Os], was found to be efficient and regioselective catalysts for the intramolecular hydroxycarboxylation of α,ω-alkynoic acids, yielding exocyclic enol lactones for ring sizes up to 7 atoms, and endocyclic enol lactones for ring sizes up to 12 atoms. They also catalysed the regioselective intermolecular hydroxycarboxylation reaction between propargylic alcohol and carboxylic acids to form β-oxo-esters. These complexes could also function as electrocatalysts in proton reduction, and evaluation of their redox potentials revealed that the iron complex was much more efficient than the ruthenium or osmium analogues.

Original language	English
Pages (from-to)	40-44
Number of pages	5
Journal	Journal of Organometallic Chemistry
Volume	889
DOIs	https://doi.org/10.1016/j.jorganchem.2019.03.019
Publication status	Published - Jul 1 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 Elsevier B.V.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

Keywords

Alkyne hydrocarboxylation
Carbamoyl
Catalysis
Group 8 metals
Proton reduction

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10.1016/j.jorganchem.2019.03.019

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title = "Group VIII carbamoyl complexes as catalysts for alkyne hydrocarboxylation and electrochemical proton reduction",

abstract = "A series of group VIII carbamoyl complexes, [M(2-NHC(O)C5H4N)(CO)2(2-SC5H4N)] [where M = Fe, Ru and Os], was found to be efficient and regioselective catalysts for the intramolecular hydroxycarboxylation of α,ω-alkynoic acids, yielding exocyclic enol lactones for ring sizes up to 7 atoms, and endocyclic enol lactones for ring sizes up to 12 atoms. They also catalysed the regioselective intermolecular hydroxycarboxylation reaction between propargylic alcohol and carboxylic acids to form β-oxo-esters. These complexes could also function as electrocatalysts in proton reduction, and evaluation of their redox potentials revealed that the iron complex was much more efficient than the ruthenium or osmium analogues.",

keywords = "Alkyne hydrocarboxylation, Carbamoyl, Catalysis, Group 8 metals, Proton reduction",

author = "Barik, {Chandan Kr} and Tessensohn, {Malcolm E.} and Webster, {Richard D.} and Leong, {Weng Kee}",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier B.V.",

year = "2019",

month = jul,

day = "1",

doi = "10.1016/j.jorganchem.2019.03.019",

language = "English",

volume = "889",

pages = "40--44",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

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TY - JOUR

T1 - Group VIII carbamoyl complexes as catalysts for alkyne hydrocarboxylation and electrochemical proton reduction

AU - Barik, Chandan Kr

AU - Tessensohn, Malcolm E.

AU - Webster, Richard D.

AU - Leong, Weng Kee

PY - 2019/7/1

Y1 - 2019/7/1

N2 - A series of group VIII carbamoyl complexes, [M(2-NHC(O)C5H4N)(CO)2(2-SC5H4N)] [where M = Fe, Ru and Os], was found to be efficient and regioselective catalysts for the intramolecular hydroxycarboxylation of α,ω-alkynoic acids, yielding exocyclic enol lactones for ring sizes up to 7 atoms, and endocyclic enol lactones for ring sizes up to 12 atoms. They also catalysed the regioselective intermolecular hydroxycarboxylation reaction between propargylic alcohol and carboxylic acids to form β-oxo-esters. These complexes could also function as electrocatalysts in proton reduction, and evaluation of their redox potentials revealed that the iron complex was much more efficient than the ruthenium or osmium analogues.

AB - A series of group VIII carbamoyl complexes, [M(2-NHC(O)C5H4N)(CO)2(2-SC5H4N)] [where M = Fe, Ru and Os], was found to be efficient and regioselective catalysts for the intramolecular hydroxycarboxylation of α,ω-alkynoic acids, yielding exocyclic enol lactones for ring sizes up to 7 atoms, and endocyclic enol lactones for ring sizes up to 12 atoms. They also catalysed the regioselective intermolecular hydroxycarboxylation reaction between propargylic alcohol and carboxylic acids to form β-oxo-esters. These complexes could also function as electrocatalysts in proton reduction, and evaluation of their redox potentials revealed that the iron complex was much more efficient than the ruthenium or osmium analogues.

KW - Alkyne hydrocarboxylation

KW - Carbamoyl

KW - Catalysis

KW - Group 8 metals

KW - Proton reduction

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DO - 10.1016/j.jorganchem.2019.03.019

M3 - Article

AN - SCOPUS:85063544685

SN - 0022-328X

VL - 889

SP - 40

EP - 44

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

Group VIII carbamoyl complexes as catalysts for alkyne hydrocarboxylation and electrochemical proton reduction

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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