Regioselective C6-Arylation of Thieno[3,2-c]pyrazole Heterocycles with Aryl Iodides

被引：0
|
作者：
Lfakir, Noura Ait [1 ,2 ,3 ]
Jismy, Badr [1 ]
Guillaumet, Gerald [2 ,4 ]
Akssira, Mohamed [3 ]
El Hakmaoui, Ahmed [3 ]
Guillot, Regis [5 ]
Tikad, Abdellatif [6 ]
Abarbri, Mohamed [1 ]
机构：
[1] Univ Tours, Fac Sci & Tech, Lab Physicochim Mat & Electrolytes Energie PCM2E, EA 6299, Ave Monge,Parc de Grandmont, F-37200 Tours, France
[2] Univ Orleans, Inst Chim Organ & Analyt ICOA, UMR CNRS 7311, BP 6759,Rue Chartres, F-45067 Orleans 2, France
[3] Univ Hassan II Casablanca, Fac Sci & Tech Mohammedia, Lab Chim Phys & Biotechnol Biomol & Mat, URAC 22, BP 146, Mohammadia 28800, Morocco
[4] Euromed Univ Fes UEMF, Euromed Fac Pharm, Euromed Res Ctr, Meknes Rd, Fes 30000, Morocco
[5] Univ Paris Saclay, CNRS UMR 8182, Inst Chim Mol & Mat Orsay, Batiment 670 Henri Moissan 1,17,Ave Sci, F-91400 Orsay, France
[6] Univ Moulay Ismail, Fac Sci, Lab Chim Mol & Subst Nat, BP 11201, Meknes, Morocco
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 12期
关键词：
Thieno[3,2-c]pyrazole; Suzuki-Miyaura cross-coupling; C-H activation; Regioselectivity; Palladium catalysis; C-H ARYLATION; CATALYZED DIRECT ARYLATION; BIOLOGICAL-ACTIVITY; BOND ARYLATION; FUNCTIONALIZATION; HETEROARYLATION; HETEROARENES; ACTIVATION; THIOPHENES; EFFICIENT;
D O I：
10.1002/adsc.202400141
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Regioselective C6-arylation of thieno[3,2-c]pyrazoles with aryl iodides as coupling partners has been developed. This strategy was performed in the presence of Pd(OAc)(2) as catalyst in combination with AgOTf as an oxidant and TFA in dimethylacetamide. In all experiments, only the C6-arylated thieno[3,2-c]pyrazole was isolated since its C5-regioisomer was not observed, indicating the high regioselectivity of this approach. The catalytic system used is compatible with a variety of 3-functionalized thieno[3,2-c]pyrazoles and iodoaryl electrophiles, providing access to 3,6-disubstituted thieno[3,2-c]pyrazoles in yields ranging from 49% to 94%.
引用
收藏
页码：2749 / 2757
页数：9
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