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Volumn 351, Issue 17, 2009, Pages 2850-2854

Iridium-catalyzed selective synthesis of 4-substituted benzofurans and indoles via directed cyclodehydration

Author keywords

C C bond formation; C H functionalization; Heterocycles; Homogeneous catalysis; Iridium

Indexed keywords


EID: 72149096779     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900570     Document Type: Article
Times cited : (92)

References (68)
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    • Classical examples of benzoheterole synthesis via cyclodehydration: a) R. Möhlau, Ber. dtsch. chem. Ges. 1881, 14, 171-175;
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    • Only a few examples of the selective synthesis of 4-substituted benzofurans by cyclodehydration were reported a) Y. Kawase, M. Takashima, Bull. Chem. Soc. Jpn. 1967, 40, 1224-1231;
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    • [4d,4g]
    • [4d,4g]
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    • Recently, iridium-catalyzed C-H arylation of heteroarenes via electrophilic metallation was reported
    • Angew. Chem. Int. Ed. 2008, 47, 7508-7510. Recently, iridium-catalyzed C-H arylation of heteroarenes via electrophilic metallation was reported:
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    • There have been several reports of heterocycle synthesis by directed cyclization. Dihydrobenzofuran and indoline synthesis by rhodium-catalyzed C-H activation/olefin insertion: a) R. K. Thalji, K. Ahrendt, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2005, 70, 6775-6781;
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    • Isobenzofuran synthesis by rhenium-catalyzed directed C-H activation/aldehyde insertion
    • b) H. Harada, R. K. Thalji, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2008, 73, 6772-6779. Isobenzofuran synthesis by rhenium-catalyzed directed C-H activation/aldehyde insertion:
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    • Harada, H.1    Thalji, R.K.2    Bergman, R.G.3    Ellman, J.A.4
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    • c) Y. Kuninobu, Y. Nishina, C. Nakagawa, K. Takai, J. Am. Chem. Soc. 2006, 128, 12376-12377. Benzoxazole synthesis by copper-catalyzed electrophilic metallation/C-O bond formation:
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    • Kuninobu, Y.1    Nishina, Y.2    Nakagawa, C.3    Takai, K.4
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    • Tanaka and co-workers independently reported a similar reaction
    • Cationic rhodium catalysis: a) K. Tsuchikama, Y. Kuwata, Y.-k. Tahara, Y. Yoshinami, T. Shibata, Org. Lett. 2007, 9, 3097-3099. Tanaka and co-workers independently reported a similar reaction:
    • (2007) Org. Lett. , vol.9 , pp. 3097-3099
    • Tsuchikama, K.1    Kuwata, Y.2    Tahara, Y.-K.3    Yoshinami, Y.4    Shibata, T.5
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    • 2O (see Scheme S1 in the Supporting Information). However, at present, we cannot determine either C-H bond cleavage or electrophilic metallation as a feasible mechanism
    • 2O (see Scheme S1 in the Supporting Information). However, at present, we cannot determine either C-H bond cleavage or electrophilic metallation as a feasible mechanism.
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    • Recently, some reports on high electron and hole transportation ability of benzodifuran derivatives were disclosed: a) H. Tsuji, C. Mitsui, L. Ilies, Y. Sato, E. Nakamura, J. Am. Chem. Soc. 2007, 129, 11902-11903;
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    • Tsuji, H.1    Mitsui, C.2    Ilies, L.3    Sato, Y.4    Nakamura, E.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.