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Volumn 16, Issue 30, 2010, Pages 8975-8979

Exclusive synthesis of β-alkylpyrroles under indium catalysis: Carbonyl compounds as sources of alkyl groups

Author keywords

Aldehydes; C C activation; Indium; Ketones; Nucleophilic substitution

Indexed keywords

ALKYL GROUPS; ALKYLPYRROLES; C-C ACTIVATION; C-C ACTIVATIONS; CARBONYL COMPOUNDS; INDIUM CATALYST; NITROGEN ATOM; NUCLEOPHILIC SUBSTITUTION; NUCLEOPHILIC SUBSTITUTIONS; REGIOSPECIFIC;

EID: 77955434940     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000733     Document Type: Article
Times cited : (26)

References (55)
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    • Despite an indirect approach, a three-step strategy starting with β-acylation of N-(arylsulfonyl) pyrroles as a key step presently seems to have been the most reliable to synthesize β-alkylpyrroles. This strategy has been first introduced by Rühe and colleagues: a) J. Rühe, T. Ezquerra, G. Wegner, Makromol. Chem. Rapid Commun. 1989, 10, 103-108;
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    • Although 4-octyne is available as a source of an alkyl group, its use imposes higher loadings of a pyrrole and indium catalyst at higher temperature, compared to standard reaction conditions
    • Although 4-octyne is available as a source of an alkyl group, its use imposes higher loadings of a pyrrole and indium catalyst at higher temperature, compared to standard reaction conditions.
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    • Carbonyl compounds have much higher skeletal and substitutional diversities than alkynes as commercial sources. See, for example, SIGMA-ALDRICH Product Catalog at
    • Carbonyl compounds have much higher skeletal and substitutional diversities than alkynes as commercial sources. See, for example, SIGMA-ALDRICH Product Catalog at http://www.sigmaaldrich.com/chemistry/chemistry-products. html?TablePage = 16273490.
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    • Disappearance of 6 followed by formation of 5 can be confirmed by GC analysis
    • Disappearance of 6 followed by formation of 5 can be confirmed by GC analysis.
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    • 2 = Me, 2a and 3a by using method A gives a 98:2 mixture of β-and α-1-phenylethyl pyrroles in 88% yield see entry 10
    • 2 = Me), 2a and 3a by using method A gives a 98:2 mixture of β-and α-(1-phenylethyl) pyrroles in 88% yield (see entry 10).
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    • 23 10mol% at 85°C for 20 h by using method A gives a 54:46 mixture of β-and α-decan-2-yl pyrroles in 28% yield
    • 3 (10mol%) at 85°C for 20 h by using method A gives a 54:46 mixture of β-and α-(decan-2-yl) pyrroles in 28% yield.
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    • 2O 1 equiv
    • 2O (1 equiv).
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    • Synthesis of dipyrrolylalkanes upon treatment of carbonyl compounds and pyrroles with acid catalysts is a well-established reaction, especially in porphyrin chemistry. For a recent review, see:, and references therein
    • Synthesis of dipyrrolylalkanes upon treatment of carbonyl compounds and pyrroles with acid catalysts is a well-established reaction, especially in porphyrin chemistry. For a recent review, see: J. S. Lindsey, Acc. Chem. Res. 2010, 43, 300-311, and references therein.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.