Copper-Catalyzed Sulfonamidation of N,N-Dimethyl Formamide via C(sp3)―H Bond Functionalization

被引：0

作者：

Ramani, Arti ^{[1
]}

Begari, Eeshwaraiah ^{[2
]}

Naveen, Togati ^{[1
]}

机构：

[1] Sardar Vallabhbhai Natl Inst Technol, Dept Chem, Surat 395007, Gujarat, India

[2] Cent Univ Gujarat, Sch Appl Mat Sci, Gandhinagar 382030, India

来源：

CHEMISTRYSELECT | 2025年 / 10卷 / 25期

关键词：

C & horbar; H bond functionalization; Copper salt; Formamidomethylation; Sulfonamides; SP(3) C-H; DEHYDROGENATIVE COUPLING REACTIONS; TRANSITION-METAL; INHIBITOR; ADJACENT; ETHERS; AZOLES; POTENT; AMIDES;

D O I：

10.1002/slct.202501889

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed a novel strategy for the direct sulfonamidation of N,N-dimethyl formamide through a copper-catalyzed C(sp3)& horbar;H functionalization reaction. This method represents a significant advancement in the field, as it does not require any exogenous acid or base, and the reaction can be completed within 2 h. A variety of N-formamidomethylated sulfonamides were synthesized in moderate to high yields. Hitherto, no prior reports have been found in the literature for the sulfonamidation of N,N-dimethyl formamide, making this reaction an important breakthrough in synthetic organic chemistry.

引用

页数：5

共 75 条

[11] Interception of Secondary Amide Ylide with Sulfonamides: Catalyst-Controlled Synthesis of N-Sulfonylamidine Derivatives [J].

Chen, Jijun ;

Long, Wenhao ;

Yang, Yonggang ;

Wan, Xiaobing .

ORGANIC LETTERS, 2018, 20 (09) :2663-2666

[12] Interception of amide ylides with sulfonamides: synthesis of (E)-N-sulfonyl amidines catalyzed by Zn(OTf)2 [J].

Chen, Jijun ;

Long, Wenhao ;

Fang, Shangwen ;

Yang, Yonggang ;

Wan, Xiaobing .

CHEMICAL COMMUNICATIONS, 2017, 53 (99) :13256-13259

[13] Direct Condensation of Sulfonamide and Formamide: Nal-Catalyzed Synthesis of N-Sulfonyl Formamidine Using TBHP as Oxidant [J].

Chen, Shulin ;

Xu, Yuan ;

Wan, Xiaobing .

ORGANIC LETTERS, 2011, 13 (23) :6152-6155

[14] Hexamethyldisilazane-Mediated Amidination of Sulfonamides and Amines with Formamides [J].

Chou, Yu-Chen ;

Lin, Wei-Han ;

Lin, Xiu-Yi ;

Kuo, Chin-Ling ;

Zeng, Wan-Qin ;

Lu, I-Chung ;

Liang, Chien-Fu .

JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (22) :15327-15332

[15] A small-molecule inhibitor of the NLRP3 inflammasome for the treatment of inflammatory diseases [J].

Coll, Rebecca C. ;

Robertson, Avril A. B. ;

Chae, Jae Jin ;

Higgins, Sarah C. ;

Munoz-Planillo, Raul ;

Inserra, Marco C. ;

Vetter, Irina ;

Dungan, Lara S. ;

Monks, Brian G. ;

Stutz, Andrea ;

Croker, Daniel E. ;

Butler, Mark S. ;

Haneklaus, Moritz ;

Sutton, Caroline E. ;

Nunez, Gabriel ;

Latz, Eicke ;

Kastner, Daniel L. ;

Mills, Kingston H. G. ;

Masters, Seth L. ;

Schroder, Kate ;

Cooper, Matthew A. ;

O'Neill, Luke A. J. .

NATURE MEDICINE, 2015, 21 (03) :248-+

[16] Friedel-Crafts Amidoalkylation via Thermolysis and Oxidative Photocatalysis [J].

Dai, Chunhui ;

Meschini, Francesco ;

Narayanam, Jagan M. R. ;

Stephenson, Corey R. J. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (09) :4425-4431

[17] Recent advances in catalytic intramolecular C-H aminations [J].

Davies, HML ;

Long, MS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (23) :3518-3520

[18] Transition metal catalyzed oxidative functionalization of carbon-hydrogen bonds [J].

Dick, AR ;

Sanford, MS .

TETRAHEDRON, 2006, 62 (11) :2439-2463

[19] Copper catalysts for radical and nonradical persulfate based advanced oxidation processes: Certainties and uncertainties [J].

Ding, Yaobin ;

Fu, Libin ;

Peng, Xueqin ;

Lei, Ming ;

Wang, Chengjun ;

Jiang, Jizhou .

CHEMICAL ENGINEERING JOURNAL, 2022, 427

[20]

Du Bois J., 2005, Chemtracts, V18, P1

← 1 2 3 4 5 6 7 8 →