Transition metal control in the reaction of alkyne-substituted phenyl iodides with terminal alkynes: Sonogashira coupling vs cyclic carbopalladation
Reaction between terminal alkynes and phenyl iodides bearing a tethered alkyne unit can be effectively controlled by the nature of a transition metal catalyst. Whereas the use of Pd(0)/Cu(I) promotes the expected Sonogashira coupling to give phenyl alkynes, the absence of the copper co-catalyst trig...
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| Published in | Tetrahedron Vol. 58; no. 44; pp. 9007 - 9018 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
28.10.2002
Elsevier |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0040-4020 1464-5416 |
| DOI | 10.1016/S0040-4020(02)01154-7 |
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| Abstract | Reaction between terminal alkynes and phenyl iodides bearing a tethered alkyne unit can be effectively controlled by the nature of a transition metal catalyst. Whereas the use of Pd(0)/Cu(I) promotes the expected Sonogashira coupling to give phenyl alkynes, the absence of the copper co-catalyst triggers a palladium-mediated cyclisation providing 1,2-dihydroacenaphthylene, 1
H,3
H-benzo[
de]isochromene, (1
Z)-1-(2-propynylidene)-2,3-dihydro-1
H-indene and (4
E)-4-(2-propynylidene)-3,4-dihydro-1
H-isochromene derivatives. In the latter Pd-catalysed two-component process, the product distribution depends on the structure of alkyne-substituted phenyl iodides, terminal alkynes and secondary amines used as solvents. The proposed reaction mechanism reflects a competitive formation of intermediary σ-(acetylide) vs π-alkyne Pd(II) complexes.
Graphic |
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| AbstractList | Reaction between terminal alkynes and phenyl iodides bearing a tethered alkyne unit can be effectively controlled by the nature of a transition metal catalyst. Whereas the use of Pd(0)/Cu(I) promotes the expected Sonogashira coupling to give phenyl alkynes, the absence of the copper co-catalyst triggers a palladium-mediated cyclisation providing 1,2-dihydroacenaphthylene, 1
H,3
H-benzo[
de]isochromene, (1
Z)-1-(2-propynylidene)-2,3-dihydro-1
H-indene and (4
E)-4-(2-propynylidene)-3,4-dihydro-1
H-isochromene derivatives. In the latter Pd-catalysed two-component process, the product distribution depends on the structure of alkyne-substituted phenyl iodides, terminal alkynes and secondary amines used as solvents. The proposed reaction mechanism reflects a competitive formation of intermediary σ-(acetylide) vs π-alkyne Pd(II) complexes.
Graphic Reaction between terminal alkynes and phenyl iodides bearing a tethered alkyne unit can be effectively controlled by the nature of a transition metal catalyst. Whereas the use of Pd(0)/Cu(I) promotes the expected Sonogashira coupling to give phenyl alkynes, the absence of the copper co-catalyst triggers a palladium-mediated cyclisation providing 1,2-dihydroacenaphthylene, 1H,3H-benzo[de]isochromene, (1Z)-1-(2-propynylidene)-2,3-dihydro-1H-indene and (4E)-4-(2-propynylidene)-3,4-dihydro-1H-isochromene derivatives. In the latter Pd-catalysed two-component process, the product distribution depends on the structure of alkyne-substituted phenyl iodides, terminal alkynes and secondary amines used as solvents. The proposed reaction mechanism reflects a competitive formation of intermediary sigma-(acetylide) vs pi-alkyne Pd(II) complexes. (C) 2002 Elsevier Science Ltd. All rights reserved. |
| ArticleNumber | 0040 |
| Author | Kollárovič, Adrian Stará, Irena G. Starý, Ivo Fiedler, Pavel Teplý, Filip Šaman, David |
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| Keywords | cyclisation aryl halides alkynes coupling reactions VINYL PALLADIUM CATALYZED CASCADE CYCLIZATION CONSTRUCTION CHEMISTRY TRIYNES PRECURSORS MOLECULES |
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| Snippet | Reaction between terminal alkynes and phenyl iodides bearing a tethered alkyne unit can be effectively controlled by the nature of a transition metal catalyst.... |
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| SubjectTerms | alkynes aryl halides Chemistry Chemistry, Organic coupling reactions cyclisation Physical Sciences Science & Technology |
| Title | Transition metal control in the reaction of alkyne-substituted phenyl iodides with terminal alkynes: Sonogashira coupling vs cyclic carbopalladation |
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