Electrochemical Diazidation of Alkenes Catalyzed by Manganese Porphyrin Complexes with Second-Sphere Hydrogen-Bond Donors

被引：17

作者：

Novaes, Luiz F. T. ^{[1
]}

Wang, Yi ^{[1
]}

Liu, Jinjian ^{[1
]}

Riart-Ferrer, Xavier ^{[2
,3
]}

Lee, Wan-Chen Cindy ^{[2
]}

Fu, Niankai ^{[1
,4
]}

Ho, Justin S. K. ^{[1
]}

Zhang, X. Peter ^{[2
]}

Lin, Song ^{[1
]}

机构：

[1] Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA

[2] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

[3] GlaxoSmithKline, Collegeville, PA 19426 USA

[4] Chinese Acad Sci, Inst Chem, Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China

来源：

ACS CATALYSIS | 2022年 / 12卷 / 22期

关键词：

electrochemistry; electrocatalysis; organic azide; vicinal diamine; metalloporphyrin; THERMOCHEMISTRY; REACTIVITY; RADICALS; ELEMENTS; CRYSTAL;

D O I：

10.1021/acscatal.2c05186

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

In this work, we report manganese porphyrin complexes for the electrocatalytic vicinal diazidation of alkenes with sodium azide. This protocol shows improved practicality over our previous work using MnBr2 catalysis in the following aspects: (1) it requires substantially lower catalyst loading (as low as 0.3 mol %), which reduces the formation of metal azide complexes and simplifies product purification; (2) the introduction of a neutral aqueous buffer prevents the generation of toxic hydrazoic acid, contributing to a safer experimental procedure; (3) the catalytic system displays improved reactivity toward unactivated terminal alkenes. Mechanistic studies support the roles of second-sphere hydrogen-bond donors in stabilizing key reaction intermediates.

引用

页码：14106 / 14112

页数：7

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