Direct palladium-catalyzed C-3 alkynylation of indoles

Tetrahedron Letters

Volumn 50, Issue 7, 2009, Pages 763-766

  Gu, Yonghong ^a   Wang, Xue min ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALKYNYL GROUP; BROMINE DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM;

ALKYNYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE;

EID: 58149147151     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.097     Document Type: Article

References (27)

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20. 1-Bromophenylacetylene (2a) was prepared by reaction of phenylacetylene with silver nitrate and N-bromosuccinimide. See:. Li L.-S., and Wu Y.-L. Tetrahedron Lett. 43 (2002) 2427
21. The reaction of 1-iodophenylacetylene with indole (1a) under various conditions did not give alkynylated indole, only homocoupled product 1,3-diyne was observed.
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23. +) 235.1361, found 235.1360.
24. The structure of 3-phenylethynylindole (3a) was established by 2D NOESY experiment, which showed cross peak between proton on C-2 at δ 7.43 (d, J = 2.4 Hz, 1H) and proton on indole nitrogen at δ 8.21 (br s, 1H, NH); additionally, 2-phenylethynylindole is a known compound, which showed proton on C-3 at δ 6.84 (d, J = 2.4 Hz, 1H). See:. Nagamochi M., Fang Y.-Q., and Lautens M. Org. Lett. 9 (2007) 2955
25. 2 and 2 equiv. NaOAc, 88% yield of 3a was obtained.
26. When the substitute of bromoalkyne 2 is alkyl group (e.g., in 1-bromo-1-octyne), no alkynylated indole was produced, only homocoupled product 1,3-diyne was observed.
27. +) 231.1048, found 231.1049.