Electrosynthesis of heterocyclic compounds by radical cyclization in environmentally friendly media

J. P. Mendes; J. M. S. S. Esperança; A. P. Esteves; M. M. Silva; M. J. Medeiros

doi:10.1149/06626.0001ecst

Electrosynthesis of heterocyclic compounds by radical cyclization in environmentally friendly media

J. P. Mendes, J. M. S. S. Esperança, A. P. Esteves, M. M. Silva, M. J. Medeiros

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution › peer-review

Abstract

We investigated the reductive intramolecular cyclization of bromopropargyl ethers derivatives, catalyzed by electrogenerated (1,4,8,11-tetramethyl-1,4,8,11-tetraaza-cyclotetradecane)nickel(I), [Ni(tmc)]⁺ as the catalysts in N,N,N-trimethyl-N-(2- hydroxyethyl)ammonium bis(trifluoromethylsulfonyl)imide,[N₁₁₁₂(OH)][NTf₂] and 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [C₂mim][NTf₂] by cyclic voltammetry and controlled-potential electrolysis. The results show that the reaction leads to the formation of the expected cyclic compounds, which are important intermediates in the synthesis of natural products with possible biological activities.

Original language	English
Title of host publication	Mechanistic Organic Electrochemistry
Publisher	Electrochemical Society Inc
Pages	1-5
Number of pages	5
Volume	66
Edition	26
ISBN (Electronic)	9781607685395
DOIs	https://doi.org/10.1149/06626.0001ecst
Publication status	Published - 2015
Event	Symposium on Mechanistic Organic Electrochemistry - 227th ECS Meeting - Chicago, United States Duration: 24 May 2015 → 28 May 2015

Conference

Conference	Symposium on Mechanistic Organic Electrochemistry - 227th ECS Meeting
Country/Territory	United States
City	Chicago
Period	24/05/15 → 28/05/15

Keywords

Electrolytic reduction
Dechlorination
Reductive dechlorination

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10.1149/06626.0001ecst

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@inproceedings{115c1218c36a4b08ac1bccb51f56cf2b,

title = "Electrosynthesis of heterocyclic compounds by radical cyclization in environmentally friendly media",

abstract = "We investigated the reductive intramolecular cyclization of bromopropargyl ethers derivatives, catalyzed by electrogenerated (1,4,8,11-tetramethyl-1,4,8,11-tetraaza-cyclotetradecane)nickel(I), [Ni(tmc)]+ as the catalysts in N,N,N-trimethyl-N-(2- hydroxyethyl)ammonium bis(trifluoromethylsulfonyl)imide,[N1112(OH)][NTf2] and 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [C2mim][NTf2] by cyclic voltammetry and controlled-potential electrolysis. The results show that the reaction leads to the formation of the expected cyclic compounds, which are important intermediates in the synthesis of natural products with possible biological activities.",

keywords = "Electrolytic reduction, Dechlorination, Reductive dechlorination",

author = "Mendes, \{J. P.\} and Esperan{\c c}a, \{J. M. S. S.\} and Esteves, \{A. P.\} and Silva, \{M. M.\} and Medeiros, \{M. J.\}",

year = "2015",

doi = "10.1149/06626.0001ecst",

language = "English",

volume = "66",

pages = "1--5",

booktitle = "Mechanistic Organic Electrochemistry",

publisher = "Electrochemical Society Inc",

edition = "26",

note = "Symposium on Mechanistic Organic Electrochemistry - 227th ECS Meeting ; Conference date: 24-05-2015 Through 28-05-2015",

}

Mendes, JP, Esperança, JMSS, Esteves, AP, Silva, MM & Medeiros, MJ 2015, Electrosynthesis of heterocyclic compounds by radical cyclization in environmentally friendly media. in Mechanistic Organic Electrochemistry. 26 edn, vol. 66, Electrochemical Society Inc, pp. 1-5, Symposium on Mechanistic Organic Electrochemistry - 227th ECS Meeting, Chicago, United States, 24/05/15. https://doi.org/10.1149/06626.0001ecst

TY - GEN

T1 - Electrosynthesis of heterocyclic compounds by radical cyclization in environmentally friendly media

AU - Mendes, J. P.

AU - Esperança, J. M. S. S.

AU - Esteves, A. P.

AU - Silva, M. M.

AU - Medeiros, M. J.

PY - 2015

Y1 - 2015

N2 - We investigated the reductive intramolecular cyclization of bromopropargyl ethers derivatives, catalyzed by electrogenerated (1,4,8,11-tetramethyl-1,4,8,11-tetraaza-cyclotetradecane)nickel(I), [Ni(tmc)]+ as the catalysts in N,N,N-trimethyl-N-(2- hydroxyethyl)ammonium bis(trifluoromethylsulfonyl)imide,[N1112(OH)][NTf2] and 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [C2mim][NTf2] by cyclic voltammetry and controlled-potential electrolysis. The results show that the reaction leads to the formation of the expected cyclic compounds, which are important intermediates in the synthesis of natural products with possible biological activities.

AB - We investigated the reductive intramolecular cyclization of bromopropargyl ethers derivatives, catalyzed by electrogenerated (1,4,8,11-tetramethyl-1,4,8,11-tetraaza-cyclotetradecane)nickel(I), [Ni(tmc)]+ as the catalysts in N,N,N-trimethyl-N-(2- hydroxyethyl)ammonium bis(trifluoromethylsulfonyl)imide,[N1112(OH)][NTf2] and 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [C2mim][NTf2] by cyclic voltammetry and controlled-potential electrolysis. The results show that the reaction leads to the formation of the expected cyclic compounds, which are important intermediates in the synthesis of natural products with possible biological activities.

KW - Electrolytic reduction

KW - Dechlorination

KW - Reductive dechlorination

UR - https://www.scopus.com/pages/publications/84940381724

U2 - 10.1149/06626.0001ecst

DO - 10.1149/06626.0001ecst

M3 - Conference contribution

AN - SCOPUS:84940381724

VL - 66

SP - 1

EP - 5

BT - Mechanistic Organic Electrochemistry

PB - Electrochemical Society Inc

T2 - Symposium on Mechanistic Organic Electrochemistry - 227th ECS Meeting

Y2 - 24 May 2015 through 28 May 2015

ER -

Electrosynthesis of heterocyclic compounds by radical cyclization in environmentally friendly media

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Keywords

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