Recently we have applied the palladium-catalyzed amination to the synthesis of ortho-bromodiarylamincs in the benzo[blthiophene series . Here we describe the application of this methodology to the amination of electron-rich or poor 3-bromobenzo[b}thiophcnes, using the same conditions for both cases

Begouin, Agathe

Ferreira, Isabel C.F.R.

Kirsch, Gilbert

Queiroz, Maria João R.P.

Biblioteca Digital do IPB

.ED 090 Wien, AUSTRIA ereofacia l selectivity . . fOl1l1ationally locked ·unds has been exten.' ~: lenes appeared 1110st' ~ynthesized from the 's) had already been to be generated. The 4 of the diazirines in : R'=OMe _ R ' "' c . CcH~ . Il ~k!l ... · 'cgard to 5-hydrox-'orate DFT (HOE) he calculations wi!! r s iOI1 of diastereos-ngs were also reaf-I be presented and :Is.: Ie Noble, W.J.; pp. 1067 - 1480. )01.42,9161. OC-44 PALLADIUM-CATALYZED AMINATION OF ELECTRON-RICH OR POOR BENZO[bjTHlENYL BROMIDES Agathe Begollin,b Isabel C. F.R. Ferreira,a Maria-lolio R P. Qlleiroz,a Gilbert Kirsch b aDepartamento de QlIimicQ, Universidade do Minho,4710-057 Braga, Portl/gal, mj rpq@quimica.uminho.pt bLaboratoire d '/ngenierie Afo/eeu/aire et Biochimie Pharmac%giqlle, Universite de l\l/et: Facllite des Sciences, lie dll Salllc): 57045 Metz. France Recently we have applied the palladium-cata lyzed amination to the synthesis of orlllo-bro-modiarylamincs in the benzo[blthiophene series 1 Here we describe the application oflhis method-ology to the amination of electron-rich or poor 3-bromobenzo[b}thiophcnes, llsing the same condi-tions for both cases. H MeOM 'N~DMe co-' I R _ # R = H, 23 h, h % S R "" C02Et, 5 h, 76 % Br ~R v--r i) PdlOAch (3 mol%), OlNAP(4 mol%), Cs2COJ (1.4 equiv.), toluene, 100 °c, Ar Th e y ields were higher, with lower heat ing times, for th e C-N coupling of 3-bromobenzo[b]thiophenc bearing an ester group in the 2-position . Using these conditions the reac-tion is compatib le with donating or withdrawing groups in the aniline. Th e diarylamincs obtained can have biological activity or can be llsed in luminescent mate-rials due to their flu orescence, which is under study. They can also be cyclized to tetracyclic het-eroaromatic systems that can a lso exhi bit biological act ivity. Thanks are due 10 IBQF-Univ. A1illho ,to the Fundar;ao Calollsle Gulbenkian (Portugal) ami to the Socrates-Erasmlls exchange programme (U.A,fillho - U.kfet;). I. Ferreira, l. e .F.R.; Quciroz. M.-J. R. P. and Kirsch, G., Tetrahedron, 2003. j9, 3737-3743. 

Palladium-catalyzed amination of electron-rich or poor benzo[b]thienyl bromides

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Palladium-catalyzed amination of electron-rich or poor benzo[b]thienyl bromides

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