Mechanochemical Conditions for Intramolecular N-O Couplings via Rhodium Nitrenoids Generated from N-Acyl Sulfonimidamides

被引：2

作者：

Pan, Shulei ^{[1
]}

Wu, Peng ^{[1
]}

Bampi, Dimitra ^{[1
]}

Ward, Jas S. ^{[2
]}

Rissanen, Kari ^{[2
]}

Bolm, Carsten ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] Univ Jyvaskyla, Dept Chem, POB 35,Survontie 9 B, Jyvaskyla 40014, Finland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2024年 / 63卷 / 50期

关键词：

Cyclization; Mechanochemistry; Nitrenoids; N-O Coupling; Rhodium; C-H AMINATION; EFFICIENT; ACCESS; AZIRIDINATION; SULFOXIMINES; PRECURSORS; ISOXAZOLES; FORCE;

D O I：

10.1002/anie.202413181

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Starting from N-acyl sulfonimidamides, mechanochemically generated rhodium nitrenoids undergo intramolecular N-O couplings to provide unprecedented 1,3,2,4-oxathiadiazole 3-oxides in good to excellent yields. The cyclization proceeds efficiently with a catalyst loading of only 0.5 mol % in the presence of phenyliodine(III) diacetate (PIDA) as oxidant. Neither an inert atmosphere nor additional heating is required in this solvent-free procedure. Under heat or blue light, the newly formed five-membered heterocycles function as nitrene precursors reacting with sulfoxides as exemplified by the imidation of dimethyl sulfoxide.

引用

页数：5

共 50 条

[1] Mechanochemical Iron-Catalyzed Nitrene Transfer Reactions: Direct Synthesis of N-Acyl Sulfonimidamides from Sulfinamides and Dioxazolones
Pan, Shulei
Mulks, Florian F.
Wu, Peng
Rissanen, Kari
Bolm, Carsten
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (05)
[2] Direct Synthesis of N-Acyl Sulfonimidamides and N-Sulfonimidoyl Amidines from Sulfonimidoyl Azides
Nandi, Ganesh Chandra
Jesin, Irfana
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (13) : 2465 - 2469
[3] CuBr/TBHP-mediated synthesis of N-acyl sulfonimidamides via the oxidative cross-coupling of sulfonimidamides and aldehydes
Nandi, Ganesh Chandra
Raju, Cijil
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (10) : 2234 - 2239
[4] Photocatalytic cross-couplings via the cleavage of N-O bonds
Zhu, Xianjin
Fu, Hua
CHEMICAL COMMUNICATIONS, 2021, 57 (76) : 9656 - 9671
[5] AN EFFICIENT METHOD FOR HYDROLYSIS OF N-MONOSUBSTITUTED AMIDES UTILIZATION OF INTRAMOLECULAR N-O ACYL MIGRATION IN HYDROXYPIVALIMIDES
TSUNODA, T
SASAKI, O
TAKEUCHI, O
ITO, S
TETRAHEDRON, 1991, 47 (24) : 3925 - 3934
[6] NBS-mediated practical cyclization of N-acyl amidines to 1,2,4-oxadiazoles via oxidative N-O bond formation
Li, Ertong
Wang, Manman
Wang, Zhen
Yu, Wenquan
Chang, Junbiao
TETRAHEDRON, 2018, 74 (35) : 4613 - 4618
[7] Intramolecular Fe(II)-Catalyzed N-O or N-N Bond Formation from Aryl Azides
Stokes, Benjamin J.
Vogel, Carl V.
Urnezis, Linda K.
Pan, Minjie
Driver, Tom G.
ORGANIC LETTERS, 2010, 12 (12) : 2884 - 2887
[8] ANOMALOUSLY LARGE STERIC INHIBITION OF INTRAMOLECULAR O,N-ACYL TRANSFER TO AMINO-ACID ESTERS
KEMP, DS
VELLACCIO, F
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (23): : 3464 - 3465
[9] Development of New Reactions Driven by N-O Bond Cleavage: from O -Acyl Hydroxylamines to Tetrodotoxin
Robins, Jacob G.
Johnson, Jeffrey S.
SYNLETT, 2023, 34 (13) : 1563 - 1572
[10] Traceless Chemical Ligation from S-, O-, and N-Acyl Isopeptides
Panda, Siva S.
Hall, C. Dennis
Oliferenko, Alexander A.
Katritzky, Alan R.
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (04) : 1076 - 1087

← 1 2 3 4 5 →