Synthesis of methanes having four different carbon substituents utilizing indium-catalyzed cleavage of carbon-pyrrolyl bonds

European Journal of Organic Chemistry

Volumn , Issue 15, 2009, Pages 2437-2440

  Tsuchimoto, Teruhisa ^a,b   Ainoya, Taku ^a   Aoki, Kazuki ^a   Wagatsuma, Tatsuya ^a   Shirakawa, Eiji ^b  

^a MEIJI UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Alkynes; C C activation; Heterocycles; Indium; Nucleophilic substitution

Indexed keywords

EID: 66149135249     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900246     Document Type: Article

References (56)

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45. The ß, ß'-adduct (4a) is obtained as the major product in the In(OTf)3-catalyzed double addition of N-methylpyrrole (2a)to 1-octyne (1a). See ref.[4] and Supporting Information.
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53. On treatment of 4a and 5a with InCl3 (10 mol-%) under the same conditions, no reaction took place. The high activity of In(OTf)3 is possibly due, at least in part, to its high Lewis acidity induced by the strong electron-withdrawing character ofthe OTf ligand.
54. Thienyl(pyrrolyl)alkanes are important units for calixthienopyrroles, as furyl(pyrrolyl)alkanes are for calixfuranopyrroles. See ref.[9]
55. After consumption of 1a upon reaction with 2a was confirmed, 5a was added to the reaction mixture. Other entries using method A also were carried out in a similar way.
56. The contamination of α-isomer 7 in several three-component reactions is likely to be related to the increasing content of α, α′-isomers among the remaining DPAs during the reaction (Table 2). For example, before and after the addition of 2-methylfuran (5a) in the reaction of Entry 1, the ratio of β, β′-, α,β′- , and α, α′-DPA changed from 86:13:1 to 82:11:7 (10min later) and then to 78:10:12 (20 min later).