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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Hashmi, A. Stephen K. Yang, Weibo Rominger, Frank |
| Description | Author Affiliation: Hashmi AS ( Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany. hashmi@hashmi.de) |
| Abstract | With the IPr ligand (IPr=1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene) on gold(I) excellent yields in the benzanellation of 2-substituted thiophenes, benzothiophenes, pyrroles, benzofurans, and indoles were achieved. The 1-siloxybut-3-ynyl side chains, incorporated in the anellation, are easily accessible by the addition of a propargyl metal reagent to a formyl group and silylation of the alcohol. This conveniently allows an anellation at the position of the formyl group under mild conditions. All reactions involve a 2,3-shift of the side chain in the anellation step and thus, provide an easy access to specific substitution patterns. Only in the case of 2-substituted indoles with their highly nucleophilic 3-position a direct hydroarylation without shift is observed. On the other hand, 3-substituted indoles give the same products as 2-substituted indoles. Then, a 3,2-shift in the indole ring system has to be involved. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 21 |
| Volume Number | 18 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2012-05-21 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Alkynes Chemistry Benzofurans Chemical Synthesis Indoles Organosilicon Compounds Thiophenes Catalysis Combinatorial Chemistry Techniques Molecular Structure Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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