An iron and copper system catalyzed C-H arylation of azoles with arylboronic acids

Synthesis (Germany)

Volumn 47, Issue 1, 2015, Pages 42-48

  Hu, Wei Ye ^a   Wang, Pei Pei ^a   Zhang, Song Lin ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

arylboronic acids; azoles; C H activation; copper and iron; environmentally friendly

Indexed keywords

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; CATALYSIS; CHEMICAL ACTIVATION; COPPER; FUNCTIONAL GROUPS;

ARYLATION REACTIONS; ARYLBORONIC ACIDS; AZOLES; BOND ACTIVATION; C-H ACTIVATION; COPPER SYSTEMS; ENVIRONMENTALLY FRIENDLY; TRIFLUOROMETHYL GROUP;

IRON;

2 (3 METHOXYPHENYL) 1,3 BENZOTHIAZOLE; 2 (3 METHOXYPHENYL) 1,3 BENZOXAZOLE; 2 (3,5 DIMETHYLPHENYL) 1,3 BENZOTHIAZOLE; 2 (3,5 DIMETHYLPHENYL) 1,3 BENZOXAZOLE; 2 (BIPHENYL 4 YL) 1,3 BENZOXAZOLE; 2 (NAPHTHALEN 2 YL) 1,3 BENZOTHIAZOLE; 2 (NAPHTHALEN 2 YL) 1,3 BENZOXAZOLE; 2 (PHENANTHREN 9 YL) 1,3 BENZOTHIAZOLE; 2 (PHENANTHREN 9 YL) 1,3 BENZOXAZOLE; 2 (PYRIMIDIN-5 YL) 1,3 BENZOXAZOLE; 2 PARA TOLYL 1,3 BENZOTHIAZOLE; 2 PARA TOLYL 1,3 BENZOXAZOLE; 2 PHENYL 1,3 BENZOTHIAZOLE; 2 PHENYL 1,3 BENZOXAZOLE; 2 [4 (TRIFLUOROMETHYL)PHENYL] 1,3 BENZOTHIAZOLE; 2 [4 (TRIFLUOROMETHYL)PHENYL] 1,3 BENZOXAZOLE; 4 (1,3 BENZOTHIAZOL 2 YL)BENZONITRILE; 4 (1,3 BENZOXAZOL 2 YL)BENZONITRILE; 4 PHENYL 2 PARA TOLYLOXAZOLE; 5 CHLORO 2 PHENYL 1,3 BENZOXAZOLE; 5 CHLORO 2 [4 (TRIFLUOROMETHYL)PHENYL] 1,3 BENZOXAZOLE; 5 CHLORO PARA TOLYL 1,3 BENZOXAZOLE; 5 NITRO 2 PHENYL 1,3 BENZOXAZOLE; 8 (1,3 BENZOXAZOL 2 YL)QUINOLINE; ARYLBORONIC ACID; BORONIC ACID DERIVATIVE; COPPER; IRON; PYRROLE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; GREEN CHEMISTRY; SYNTHESIS;

EID: 84919667634     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0034-1379073     Document Type: Article

References (14)

1. Tzanopoulou S., Sagnou M., Paravatou-Petsotas M., Gourni E., Loudos G., Xanthopoulos S., Lafkas D., Kiaris H., Varvarigou A., Pirmettis I. C., Papadopoulos M., Pelecanou M. J. Med. Chem.: 2010; 53 4633
2. Van Zandt M. C., Jones M. L., Gunn D. E., Geraci L. S., Jones J. H., Sawicki D. R., Sredy J., Jacot J. L., DiCioccio A. T., Petrova T., Mitschler A., Podjarny A. D. J. Med. Chem.: 2005; 48 3141
3. Katz L. J. Am. Chem. Soc.: 1953; 75 712
4. Dalvie D. K., Kalgutkar A. S., Khojasteh-Bakht S. C., Obach R. S., O'Donnell J. P. Chem. Res. Toxicol.: 2002; 15 269
5. Boeini H. Z., Najafabadi K. H. Eur. J. Org. Chem.: 2009; 4926
6. Riadi Y., Mamouni R., Azzalou R., El Haddad M., Routier S., Guillaumet G., Lazar S. Tetrahedron Lett.: 2011; 52 3492
7. Wang H., Wang L., Shang J., Li X., Wang H., Gui J., Lei A. Chem. Commun.: 2012; 48 76
8. Bonnamour J., Bolm C. Org. Lett.: 2008; 10 2665
9. Yuan Y., Thomé I., Kim S. H., Chen D., Beyer A., Bonnamour J., Zuidema E., Chang S., Bolm C. Adv. Synth. Catal.: 2010; 352 2892
10. Miyaura N., Suzuki A. Chem. Rev.: 1995; 95 2457
11. Littke A. F., Fu G. C. Angew. Chem. Int. Ed.: 2002; 41 4176
12. King A. E., Brunold T. C., Stahl S. S. J. Am. Chem. Soc.: 2009; 131 5044
13. Ribas X., Calle C., Poater A., Casitas A., Gómez L., Xifra R., Parella T., Benet-Buchholz J., Schweiger A., Mitrikas G., Solà M., Llobet A., Stack T. D. P. J. Am. Chem. Soc.: 2010; 132 12299
14. Casitas A., King A. E., Parella T., Costas M., Stahl S. S., Ribas X. Chem. Sci.: 2010; 1 326