A mild and efficient carboxylate-directed C-H arylation of aryl carboxylic acids with iodobenzenes in water

Tetrahedron Letters

Volumn 56, Issue 2, 2015, Pages 475-477

  Xu, Zhongmiao ^a   Yang, Ting ^a   Lin, Xichen ^a   Elliott, John D ^a   Ren, Feng ^a  

^a GLAXOSMITHKLINE   (China)

Author keywords

Aqueous micelle; Aryl carboxylic acid; C H arylation; C H functionalization; Carboxylate directed; Tween 20

Indexed keywords

2 NAPHTHOIC ACID; CARBOXYLIC ACID DERIVATIVE; CETRIMIDE; IODOBENZENE; ORGANIC SOLVENT; PALLADIUM; POLYSORBATE 20; TRIFLUOROACETIC ACID; WATER;

ARTICLE; ARYLATION; CARBOXYLATE DIRECTED C H ARYLATION; CATALYSIS; CATALYST; COVALENT BOND; CROSS COUPLING REACTION; LOW TEMPERATURE; MICELLIZATION; SOLUBILITY; STEREOSPECIFICITY;

EID: 84949116322     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.12.001     Document Type: Article

References (20)

1. For selected recent reviews on C-H functionalization, see: X. Chen, K.M. Engle, D.-H. Wang, and J.-Q. Yu Angew. Chem., Int. Ed. 48 2009 5094
2. J. Wencel-Delord, T. Droge, F. Liu, and F. Glorius Chem. Soc. Rev. 40 2011 4740
3. B.-J. Li, and Z.-J. Shi Chem. Soc. Rev. 41 2012 5588
4. P.B. Arockiam, C. Bruneau, and P.H. Dixneuf Chem. Rev. 112 2012 5879
5. R. Rossi, F. Bellina, M. Lessi, and C. Manzini Adv. Synth. Catal. 356 2014 17
6. R. Giri, S. Thapa, and A. Kafle Adv. Synth. Catal. 356 2014 1395
7. For recent reviews, see K.M. Engle, T.-S. Mei, M. Wasa, and J.-Q. Yu Acc. Chem. Res. 45 2012 788
8. S.D. Sarkar, W. Liu, S.I. Kozhushkov, and L. Ackermann Adv. Synth. Catal. 356 2014 1461
9. J. Cornella, M. Righi, and I. Larrosa Angew. Chem., Int. Ed. 50 2011 9429
10. C. Arroniz, A. Ironmonger, G. Rassias, and I. Larrosa Org. Lett. 15 2013 910
11. R. Giri, N. Maugel, J.-J. Li, D.-H. Wang, S.P. Breazzano, B. Lindsey, L.B. Saunders, and J.Q. Yu J. Am. Chem. Soc. 129 2007 3510
12. H.A. Chiong, Q.-N. Pham, and O. Daugulis J. Am. Chem. Soc. 129 2007 9879
13. G. Shi, and Y. Zhang Adv. Synth. Catal. 356 2014 1419
14. Z. Wu, S. Chen, C. Hu, Z. Li, H. Xiang, and X. Zhou ChemCatChem 5 2013 2839
15. B. Li, and P.H. Dixneuf Chem. Soc. Rev. 42 2013 5744
16. C.-J. Li, and L. Chen Chem. Soc. Rev. 35 2006 68
17. T. Dwars, E. Paetzold, and G. Oehme Angew. Chem., Int. Ed. 44 2005 7174
18. T. Nishikata, A.R. Abela, and B.H. Lipshutz Angew. Chem., Int. Ed. 49 2010 781
19. F. Szabó, J. Daru, D. Simkó, T.Z. Nagy, A. Stirling, and Z. Novák Adv. Synth. Catal. 355 2013 685
20. O. Daugulis, H.-Q. Do, and D. Shabashov Acc. Chem. Res. 42 2009 1074