1H-1,2,3-Triazol-5-ylidenes as Catalytic Organic Single-Electron Reductants

被引：8

作者：

Abdellaoui, Mehdi ^{[1
]}

Oppel, Kai ^{[1
]}

Vianna, Adam ^{[1
]}

Soleilhavoup, Michele ^{[1
]}

Yan, Xiaoyu ^{[2
]}

Melaimi, Mohand ^{[1
]}

Bertrand, Guy ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem & Biochem, UCSD CNRS Joint Res Lab IRL3555, La Jolla, CA 92093 USA

[2] Renmin Univ China, Dept Chem, Key Lab Adv Light Convers Mat & Biophoton, Beijing 100872, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2024年 / 146卷 / 05期

关键词：

HETEROCYCLIC CARBENE CATALYSIS; HYDROGEN CARBONATES; FACILE PREPARATION; METAL-COMPLEXES; DONORS; IMIDAZOLIUM; SOLUBILITY; NHCS; CO2;

D O I：

10.1021/jacs.3c14360

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Most of the known single-electron reductants are either metal based reagents, used in a stoichiometric amount, or a combination of an organic species and a photocatalyst. Here we report that 1H-1,2,3-triazol-5-ylidenes act not only as stoichiometric one-electron donors but also as catalytic organic reducing agents, without the need of a photocatalyst. As a proof of concept, we studied the reduction of quinones, which are well-known electron conveyors that are involved in various biological and industrial processes. This work also provides experimental evidence for the formation of a bis-(triazolium)-carbonate adduct, which acts as the resting state of the catalytic cycle and as the carbene reservoir.

引用

页码：2933 / 2938

页数：6

共 50 条

[21] Synthesis and antimicrobial activity of 5-(1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazole derivatives
Konstantin Yu. Krolenko
Sergiy V. Vlasov
Irina A. Zhuravel
Chemistry of Heterocyclic Compounds, 2016, 52 : 823 - 830
[22] Synthesis and antimicrobial activity of 5-(1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazole derivatives
Krolenko, Konstantin Yu.
Vlasov, Sergiy V.
Zhuravel, Irina A.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (10) : 823 - 830
[23] Synthesis of [5-(1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazol-2-yl]pyridines
Pokhodylo, N. T.
Shiika, O. Ya.
Matiichuk, V. S.
Obushak, N. D.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (03) : 417 - 421
[24] 5-Chloro-8-{[1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}quinoline
Luna Parada, Luz Karime
Kouznetsov, Vladimir V.
MOLBANK, 2019, (01)
[25] Synthesis of [5-(1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazol-2-yl]pyridines
N. T. Pokhodylo
O. Ya. Shiika
V. S. Matiichuk
N. D. Obushak
Russian Journal of Organic Chemistry, 2010, 46 : 417 - 421
[26] Azirine-triazole hybrids: selective synthesis of 5-(2H-azirin-2-yl)-, 5-(1H-pyrrol-2-yl)-1H-1,2,3-triazoles and 2-(5-(2H-azirin-2-yl)-1H-1,2,3-triazol-1-yl)pyridines
Krivolapova, Yulia, V
Tomashenko, Olesya A.
Funt, Liya D.
Spiridonova, Dar'ya, V
Novikov, Mikhail S.
Khlebnikov, Alexander F.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (27) : 5434 - 5443
[27] [1-(3-Chlorophenyl)-1H-1,2,3-triazol-4-yl]methanol hemihydrate
Boechat, Nuebia
Ferreira, Maria de Lourdes G.
Bastos, Monica M.
Wardell, James L.
Wardell, Solange M. S. V.
Tiekink, Edward R. T.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2934 - U495
[28] Substituted 4-(1H-1,2,3-triazol-1-yl)-tetrafluorobenzoates: Selective synthesis and structure
Solodukhin, Nikolai N.
Borisova, Nataliya E.
Churakov, Andrei V.
Zaitsev, Kirill V.
JOURNAL OF FLUORINE CHEMISTRY, 2016, 187 : 15 - 23
[29] Defining surface properties of fluorous bis(1H-1,2,3-triazol-4-ylmethyl) ethers
Francis, Dominic V.
Harper, Jason B.
Gioia, Simon
Lamb, Robert N.
Read, Roger W.
JOURNAL OF FLUORINE CHEMISTRY, 2016, 183 : 36 - 43
[30] 1-Amino-3-(1H-1,2,3-triazol-1-yl)propylphosphonates as Acyclic Analogs of Nucleotides
Glowacka, Iwona E.
Balzarini, Jan
Piotrowska, Dorota G.
ARCHIV DER PHARMAZIE, 2014, 347 (07) : 496 - 505

← 1 2 3 4 5 →