TY - JOUR
T1 - Palladium-catalyzed cross-alkynylation of aryl bromides by sodium tetraalkynylaluminates
AU - Gelman, Dmitri
AU - Tsvelikhovsky, Dmitry
AU - Molander, Gary A.
AU - Blum, Jochanan
PY - 2002/9/6
Y1 - 2002/9/6
N2 - Sodium tetraalkynylaluminates (1-4), prepared from NaAlH4 and terminal alkynes, cross-couple with aryl bromides in the presence of Pd(0) and Pd(II) catalysts. The reactions take place in boiling THF or DME. The process is applicable to both homo- and heterocyclic aryl bromides and can be used for conversion of polybromo compounds into polyalkynes. The reactions are high yielding and selective, free of undesired homocoupling and hydrogenolysis processes. The reagents selectively react with the ring-bound bromine atoms but do not affect chloro, cyano, triflate, or ester functions.
AB - Sodium tetraalkynylaluminates (1-4), prepared from NaAlH4 and terminal alkynes, cross-couple with aryl bromides in the presence of Pd(0) and Pd(II) catalysts. The reactions take place in boiling THF or DME. The process is applicable to both homo- and heterocyclic aryl bromides and can be used for conversion of polybromo compounds into polyalkynes. The reactions are high yielding and selective, free of undesired homocoupling and hydrogenolysis processes. The reagents selectively react with the ring-bound bromine atoms but do not affect chloro, cyano, triflate, or ester functions.
UR - http://www.scopus.com/inward/record.url?scp=0037031690&partnerID=8YFLogxK
U2 - 10.1021/jo020169q
DO - 10.1021/jo020169q
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C2 - 12201745
AN - SCOPUS:0037031690
SN - 0022-3263
VL - 67
SP - 6287
EP - 6290
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 18
ER -