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

共 50 条

[31] Facile Synthesis of Z-Alkenes via Uphill Catalysis
Singh, Kamaljeet
Staig, Shannon J.
Weaver, Jimmie D.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (14) : 5275 - 5278
[32] Photochemical Halogen-Bonding Promoted Synthesis of Vinyl Sulfones via Vinyl and Sulfonyl Radicals
Jiang, Zhou
You, Ke
Wu, Haibo
Xu, Mengyu
Wang, Tao
Luo, Jin
ORGANIC LETTERS, 2024, 26 (03) : 636 - 641
[33] One-pot synthesis of α-methyl vinyl sulfones from ethyl phenyl sulfones
Lee, JW
Lee, CW
Jung, JH
Oh, DY
SYNTHETIC COMMUNICATIONS, 2000, 30 (02) : 279 - 283
[34] SYNTHESIS VIA VINYL SULFONES .59. SYNTHESIS OF BETA-SUBSTITUTED CYCLOPENTENONES VIA CARBON ALKYLATION OF METALATED GAMMA-METHOXYCYCLOPENTENYL PHENYLSULFONYL ANION
KIM, SH
JIN, ZD
FUCHS, PL
TETRAHEDRON LETTERS, 1995, 36 (26) : 4537 - 4538
[35] Ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones
Gao, Xiaofang
Pan, Xiaojun
Gao, Jian
Huang, Huawen
Yuan, Gaoqing
Li, Yingwei
CHEMICAL COMMUNICATIONS, 2015, 51 (01) : 210 - 212
[36] Isomerisation of Vinyl Sulfones for the Stereoselective Synthesis of Vinyl Azides
Collins, Niall
Connon, Robert
Sanchez-Sanz, Goar
Evans, Paul
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (39) : 6228 - 6235
[37] Synthesis of γ-keto sulfones through sulfonylation/acylation of alkenes merging NHC- and photo-catalysis
Sun, Xu
Zhang, Gan
Ye, Bo
Yang, Wen-Chao
Wang, Lei
Xie, Xiaoyu
Zhang, Yicheng
Liu, Jie
MOLECULAR CATALYSIS, 2024, 569
[38] SULFONES IN HORNER-WITTIG SYNTHESIS OF ALKENES
ELLINGSEN, PO
UNDHEIM, K
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1979, 33 (07): : 528 - 530
[39] Electrosynthesis of vinyl sulfones from alkenes and sulfonyl hydrazides mediated by KI: An electrochemical mechanistic study
Terent'ev, Alexander O.
Mulina, Olga M.
Pirgach, Dmitry A.
Ilovaisky, Alexey I.
Syroeshkin, Mikhail A.
Kapustina, Nadezhda I.
Nikishin, Gennady I.
TETRAHEDRON, 2017, 73 (49) : 6871 - 6879
[40] FACILE SYNTHESIS OF VINYL SULFONES FROM METHYL PHENYL SULFONE
LEE, JW
OH, DY
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1989, 10 (04) : 392 - 392

← 1 2 3 4 5 →