Pd-catalyzed Heck reactions of aryl bromides with 1,2-diarylethenes
A catalytic system composed of Pd(OAc)2 and P(o-tol)3 was found to be effective for the Heck reaction of aryl bromides with diarylethylenes. Using K2CO3 as a base and DMF as a solvent, trisubstituted olefins were obtained in good to excellent yields. Aryl bromides containing an electron-withdrawing group in para position were less reactive for the Heck coupling reaction and gave substantial amount of homocoupling by-product suggesting that oxidative addition is not the rate-determining step. Electron withdrawing group substituent in the para position of stilbene affects the regioselectivity of the reaction. In this case, the phenyl group from the Ph-Pd complex migrates preferentially to the same carbon of the double bond to which the phenyl is bonded. Finally, a one pot sequential double Heck arylation of styrene was performed, giving trisubstituted olefin with an overall yield of 73%.
| Main Authors: | , , |
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| Format: | Digital revista |
| Language: | English |
| Published: |
Sociedade Brasileira de Química
2011
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| Online Access: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011000700026 |
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