Visible-Light-Promoted Synthesis of Vinyloxaziridines from Conjugated Carbonyls

被引：1

作者：

Austin, Brooke E. ^{[1
]}

Palner, Ryan P. ^{[1
]}

Tobias, Elissa M. ^{[1
]}

Madiu, Rufai ^{[1
]}

Doran, Erin L. ^{[1
]}

Doran, Jenna M. ^{[1
]}

Howard, Amari M. ^{[1
]}

Stroud, James L. ^{[1
]}

Rossi, Morgan E. ^{[1
]}

Moskovitz, Dylan A. ^{[1
]}

Rivera, Dominic A. ^{[1
]}

Mullen, Michael D. ^{[1
]}

Zinsky, Amy H. ^{[1
]}

Rosario, Rose A. ^{[1
]}

Moura-Letts, Gustavo ^{[1
]}

机构：

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

来源：

SYNLETT | 2024年 / 35卷 / 03期

基金：

美国国家科学基金会;

关键词：

photoisomerization; oxaziridines; nitrones; visible light; single-electron transfer; PHOTOREDOX CATALYSIS; PRIMARY AMINES; GAS-PHASE; AB-INITIO; OXAZIRIDINES; REARRANGEMENT; OXIDATION; CYCLOADDITION; NITRONES; AMINOHYDROXYLATION;

D O I：

10.1055/a-2153-6687

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the first visible-light-promoted synthesis of vinyloxaziridines from simple conjugated nitrones. We have found that vinyl nitrones formed by the condensation reaction between conjugated carbonyls and hydroxylamines undergo visible-light-promoted energy transfer isomerization to the respective vinyloxaziridines in very high yields and selectivities. The reaction scope expands to a large array of substitution patterns, and evidence indicates that the proposed energy-transfer pathway is the predominant mechanism for this transformation.

引用

页码：325 / 329

页数：5

共 50 条

[21] Visible-light-promoted synthesis of phenanthridines via an intermolecular isocyanide insertion reaction
Zhou, Hui
Deng, Xin Zhao
Zhang, Ai Hua
Tan, Ren Xiang
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (44) : 10407 - 10414
[22] Synthesis of Tetracyclic Quinazolinones Using a Visible-Light-Promoted Radical Cascade Approach
Han, Yue-Yue
Jiang, Heng
Wang, Ruzhi
Yu, Shouyun
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) : 7276 - 7281
[23] Recent Advances in Visible-Light-Promoted Transformation of Alkyl Boron Compounds
Shi, Dunfa
Wang, Lu
Xia, Chungu
Liu, Chao
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (11) : 3605 - 3619
[24] Visible-Light-Promoted Decarboxylative Alkylation/Cyclization of Vinylcycloalkanes
Liu, Yu
Sui, Jia-Li
Yu, Wen-Qin
Xiong, Bi-Quan
Tang, Ke-Wen
Zhong, Long-Jin
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13) : 8563 - 8575
[25] Visible-Light-Promoted Arylation Reactions Photocatalyzed by Bismuth(III) Oxide
Buglioni, Laura
Riente, Paola
Palomares, Emilio
Pericas, Miquel A.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (46) : 6986 - 6990
[26] Visible-Light-Promoted Metal-Free Aerobic Hydroxyazidation Alkenes
Yang, Bo
Lu, Zhan
ACS CATALYSIS, 2017, 7 (12): : 8362 - 8365
[27] Visible-light-promoted Cascade Reaction of Acryloylbenzamides with Carboxylic Acids: Metal-free Synthesis of Isoquinolinediones
Cai, Xingxing
Fu, Jiahui
Gu, Li
Cheng, Dongping
Wang, Hong
Xu, Xiaoliang
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (08)
[28] Visible-Light-Promoted Click [3+2] Cycloaddition of Aziridine with Alkyne: An Efficient Synthesis of Dihydropyrrolidine
Kapoor, Ritu
Chawla, Ruchi
Verma, Ankit
Keshari, Twinkle
Siddiqui, I. R.
SYNLETT, 2023, 34 (13) : 1621 - 1625
[29] Visible-light-promoted aerobic oxidative cyclization to access 1,3,4-oxadiazoles from aldehydes and acylhydrazides
Yadav, Arvind K.
Yadav, Lal Dhar S.
TETRAHEDRON LETTERS, 2014, 55 (13) : 2065 - 2069
[30] Visible-Light-Promoted Atom Transfer Radical Cyclization of Unactivated Alkyl Iodides
Shen, Yangyang
Cornella, Josep
Julia-Hernandez, Francisco
Martin, Ruben
ACS CATALYSIS, 2017, 7 (01): : 409 - 412

← 1 2 3 4 5 →