Synthesis of Vinyl Sulfones from Substituted Alkenes via Molybdooxaziridine Catalysis

被引：0

作者：

Doran, Erin L. ^{[1
]}

Doran, Jenna M. ^{[1
]}

Pinarci, Ali A. ^{[1
]}

Rossi, Morgan E. ^{[1
]}

Madiu, Rufai ^{[1
]}

Howard, Amari M. ^{[1
]}

Stroud, James L. ^{[1
]}

Rivera, Dominic A. ^{[1
]}

Moskovitz, Dylan A. ^{[1
]}

Singer, Alyssa N. ^{[1
]}

Finneran, Steven J. ^{[1
]}

Moura-Letts, Gustavo ^{[1
]}

机构：

[1] Rowan Univ, Chem & Biochem Dept, 201 Mullica Hill Rd, Glassboro, NJ 08028 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2025年

基金：

美国国家科学基金会;

关键词：

Metallooxaziridines; atom transfer radical additions; vinyl sulfones; homogeneous catalysis; TRANSFER RADICAL-ADDITION; STEREOSELECTIVE-SYNTHESIS; ARYL; METALLOOXAZIRIDINES; SULFONYLATION; NUCLEOPHILES; INHIBITORS; CHEMISTRY; MICHAEL; LIGHT;

D O I：

10.1002/ejoc.202401335

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we report the MoO2Dipic promoted sulfonation of alkenes using N-Ts-hydroxylamine as the quantitative source of Ts. The reaction works with high yields and stereoselectivities for styrenes with a wide variety of substitution patterns. A novel atom transfer radical addition mechanism involving the formation of molybdooxaziridine complex 1 as the active catalyst, difunctionalization with Ts-NO, followed by oxidation, and then elimination as the rate-determining-step for the formation of vinylsulfone 3 has been proposed. Initial kinetic and mechanistic data indicates the formation of Ts-NO and provides evidence for the proposed mechanism.

引用

页数：7

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