Let the Best Ring Win: Selective Macrocycle Formation through Pd-Catalyzed or Cu-Mediated Alkyne Homocoupling

Competition is good: The reported “Pd” homocoupling procedure is now a viable alternative to the traditional Cu‐mediated reaction for the formation of diacetylenic macrocycles. From the same starting material, use of Cu(OAc)2 or [PdCl2(dppe)]/I2 (dppe=1,2‐bis(diphenylphosphanyl)ethane) leads to sele...

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Published inAngewandte Chemie (International ed.) Vol. 43; no. 13; pp. 1694 - 1697
Main Authors Marsden, Jeremiah A., Miller, Jeremie J., Haley, Michael M.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 19.03.2004
WILEY‐VCH Verlag
Wiley
Subjects
alkynes
Alkynes - chemical synthesis
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Copper - chemistry
Cyclization
CC coupling
dehydroannulenes
homocoupling
macrocycles
Macrocyclic Compounds - chemical synthesis
Macrocyclic Compounds - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Palladium - chemistry
Physical Sciences
Science & Technology
C-C coupling
DEHYDROBENZOANNULENES
ROUTE
DONOR
CRYSTAL-STRUCTURE
alkynes
homocoupling
macrocycles
NONLINEAR-OPTICAL PROPERTIES
ACETYLENIC CYCLOPHANES
clehydroannulenes
DERIVATIVES
CYCLIZATION
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Summary:Competition is good: The reported “Pd” homocoupling procedure is now a viable alternative to the traditional Cu‐mediated reaction for the formation of diacetylenic macrocycles. From the same starting material, use of Cu(OAc)2 or [PdCl2(dppe)]/I2 (dppe=1,2‐bis(diphenylphosphanyl)ethane) leads to selective formation of either the bis[15]‐ or bis[14]annulenes (see scheme).
Bibliography:istex:08BFB9AE38B1675FF4C613A81D5C4B47E1516837
This work was supported by the National Science Foundation (CHE-0104854). J.A.M. acknowledges the NSF for an IGERT fellowship. J.J.M. acknowledges the UO Ronald E. McNair Scholars Program for a summer research fellowship.
ark:/67375/WNG-3077X56K-B
ArticleID:ANIE200353043
This work was supported by the National Science Foundation (CHE‐0104854). J.A.M. acknowledges the NSF for an IGERT fellowship. J.J.M. acknowledges the UO Ronald E. McNair Scholars Program for a summer research fellowship.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200353043