Palladium-catalyzed cross-alkynylation of aryl bromides by sodium tetraalkynylaluminates

Dmitri Gelman; Dmitry Tsvelikhovsky; Gary A. Molander; Jochanan Blum

doi:10.1021/jo020169q

Palladium-catalyzed cross-alkynylation of aryl bromides by sodium tetraalkynylaluminates

Dmitri Gelman, Dmitry Tsvelikhovsky, Gary A. Molander, Jochanan Blum^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

44 Scopus citations

Abstract

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.

Original language	American English
Pages (from-to)	6287-6290
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	67
Issue number	18
DOIs	https://doi.org/10.1021/jo020169q
State	Published - 6 Sep 2002

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title = "Palladium-catalyzed cross-alkynylation of aryl bromides by sodium tetraalkynylaluminates",

abstract = "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.",

author = "Dmitri Gelman and Dmitry Tsvelikhovsky and Molander, {Gary A.} and Jochanan Blum",

year = "2002",

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journal = "Journal of Organic Chemistry",

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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

M3 - Article

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 -

Palladium-catalyzed cross-alkynylation of aryl bromides by sodium tetraalkynylaluminates

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