Iron(II)-Based Metalloradical Activation: Switch from Traditional Click Chemistry to Denitrogenative Annulation

被引:65
作者
Roy, Satyajit [1 ]
Khatua, Hillol [1 ]
Das, Sandip Kumar [1 ]
Chattopadhyay, Buddhadeb [1 ]
机构
[1] Ctr Biomed Res CBMR, Div Mol Synth & Drug Discovery, SGPGIMS Campus,Raebareli Rd, Lucknow 226014, Uttar Pradesh, India
关键词
annulations; iron; nitrogen heterocycles; nitrenes; radicals; C-H AMINATION; SUBSTITUTED DIAZO REAGENTS; ASYMMETRIC RADICAL CYCLOPROPANATION; C(SP(3))-H BONDS; CATALYSIS; AZIDES; ALKENES; AZIRIDINATION; CONSTRUCTION; TRANSANNULATION;
D O I
10.1002/anie.201904702
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A unique concept for the intermolecular denitrogenative annulation of 1,2,3,4-tetrazoles and alkynes was discovered by using a catalytic amount of Fe(TPP)Cl and Zn dust. The reaction precludes the traditional, more favored click reaction between an organic azide and alkynes, and instead proceeds by an unprecedented metalloradical activation. The method is anticipated to advance access to the construction of important basic nitrogen heterocycles, which will in turn enable discoveries of new drug candidates.
引用
收藏
页码:11439 / 11443
页数:5
相关论文
共 59 条
[1]  
[Anonymous], 2013, ANGEW CHEM, V125, P5417
[2]  
[Anonymous], 2018, ANGEW CHEM, V130, P146
[3]  
[Anonymous], 2013, ANGEW CHEM, V125, P1411
[4]  
[Anonymous], 2012, ANGEW CHEM, V124, P886
[5]  
[Anonymous], 2016, ANGEW CHEM, V128, P11776
[6]  
[Anonymous], 2010, ANGEW CHEM, V122, P10390
[7]  
[Anonymous], 2018, ANGEW CHEM, V130, P5595
[8]   Transition-Metal-Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems [J].
Chattopadhyay, Buddhadeb ;
Gevorgyan, Vladimir .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) :862-872
[9]   Fused Tetrazoles as Azide Surrogates in Click Reaction: Efficient Synthesis of N-Heterocycle-Substituted 1,2,3-Triazoles [J].
Chattopadhyay, Buddhadeb ;
Vera, Claudia I. Rivera ;
Chuprakov, Stepan ;
Gevorgyan, Vladimir .
ORGANIC LETTERS, 2010, 12 (09) :2166-2169
[10]   Bromoporphyrins as versatile synthons for modular construction of chiral porphyrins: Cobalt-catalyzed highly enantioselective and diastereoselective cyclopropanation [J].
Chen, Y ;
Fields, KB ;
Zhang, XP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (45) :14718-14719