PsfMiunr-medistd haaoennufstion ofinterred tdkynes withresin-bound o-iodomdm ""e dwivadves 4 or 5a pmided diverse trisubstituted indoles 6 in goodyields. The fecile reactionof trirnethylsilylalkynes sfforded resin-bound precursors usefrdforobtainirrg other 2-substituted indolederivadves, suchas 12.
Solid phase synthesis of 2-substituted benzofurans via the palladium-catalysed heteroannulation of acetylenes
β Scribed by Daniele Fancelli; Maria Chiara Fagnola; Dino Severino; Angelo Bedeschi
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 279 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The copper/palladium-promoted heteroannulation of terminal acetylenic compounds in the presence of resin bound ortho-hydroxy aryl iodides is described. The process produces 2-substituted benzofuran derivatives in good yield and high purity.
π SIMILAR VOLUMES
High yklds for the cleavage reaction of Fmoc-protected peptide segments fmn an allylic handle may be obtained using tributyltin hydride in the jmsence of (ph3P)PdQ in a 1:l mixture of DMF/DCM. Altematively tbe cleavage reacdon may be carried out using NMA as nuclecpbile in a 2:2:1 mixture of DMSOfl'
2-Aryl-3-alkylindoles were prepared on solid phase via palladium-mediated heteroannulation of 1-alkyl-2-(trimethylsilyl)acetylene with amide resin-bound o-iodoaniline 1, followed by transformation of trimethylsilyl to iodide and then Suzuki coupling reactions. Traceless synthesis of symmetrical and