Reductive Heck cyclization versus δ-carbon elimination/decarboxylation: synthesis of dihydroindole and indoles from Baylis-Hillman adducts

Tetrahedron Letters

Volumn 50, Issue 26, 2009, Pages 3154-3157

  Kim, Hoo Sook ^a   Lee, Hyun Seung ^a   Kim, Se Hee ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

Carbon elimination; Baylis Hillman adduct; Dihydroindole; Indole; Palladium; Reductive Heck cyclization

Indexed keywords

ANILINE DERIVATIVE; CARBON; INDOLE DERIVATIVE; PALLADIUM;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DECARBOXYLATION; ELIMINATION REACTION; HECK REACTION; SYNTHESIS;

EID: 67349142177     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.127     Document Type: Article

References (31)

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26. 2 and Pd(0) to form 3a would be also possible. For this type of reductive cleavage process involving decarboxylation, see:. Harayama H., Kuroki T., Kimura M., Tanaka S., and Tamaru Y. Angew. Chem., Int. Ed. 36 (1997) 2352-2354
27. 3SnH, benzene, reflux, 2 h) in 71% yield also. However, due to the toxicity of tin metal and the fact that more than equivalent amounts of tin compound have to be used, reductive Heck reaction can be regarded as a superior way than the radical process.
28. 3, 300 MHz) δ 1.39 (br t, J = 6.6 Hz, 3H), 4.33 (br s, 2H), 4.82 (br s, 2H), 6.84 (t, J = 3.0 Hz, 1H), 7.01 (t, J = 7.5 Hz, 1H), 7.22-7.42 (m, 6H), 7.52 (d, J = 7.5 Hz, 1H), 7.97 (s, 1H)
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