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Volumn 54, Issue 36, 2015, Pages 10613-10617

Rhodium-Catalyzed C-H Annulation of Nitrones with Alkynes: A Regiospecific Route to Unsymmetrical 2,3-Diaryl-Substituted Indoles

Author keywords

alkynes; C H activation; indoles; nitrones; rhodium

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; POLYCYCLIC AROMATIC HYDROCARBONS; REGIOSELECTIVITY; RHODIUM; SUBSTITUTION REACTIONS;

EID: 84940052323     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201503997     Document Type: Article
Times cited : (118)

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    • The high KIE values (2.6-4.0) observed in this reaction suggest that slow hydrogen abstraction might occur after the electrophilic attack of Rh on the N-phenyl ring in the C-H activation process. For similar observations, see Ref. [13]; see also:, X. Zhao, C. S. Yeung, V. M. Dong, J. Am. Chem. Soc. 2010, 132, 5837.
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    • With 0.25 equivalents of [{CpRhCl2}2] (50 mol % Rh), 4 a was isolated in 35 % yield, and no 3 a was detected.
    • With 0.25 equivalents of [{CpRhCl2}2] (50 mol % Rh), 4 a was isolated in 35 % yield, and no 3 a was detected.
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    • Use of Fe(OAc)2 or Mn(OAc)2 (1 equiv) instead of Cu(OAc)2 did not afford any product. The replacement of Cu(OAc)2 with Cu(OTf)2 (1 equiv) only gave 3 a in 30 % yield.
    • The use of Fe(OAc)2 or Mn(OAc)2 (1 equiv) instead of Cu(OAc)2 did not afford any product. The replacement of Cu(OAc)2 with Cu(OTf)2 (1 equiv) only gave 3 a in 30 % yield.
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    • During the preparation of this manuscript, the rhodium(III)-catalyzed cyclization of aryl nitrones with diaryl alkynes was reported to afford indolines in the absence of copper salts.
    • During the preparation of this manuscript, the rhodium(III)-catalyzed cyclization of aryl nitrones with diaryl alkynes was reported to afford indolines in the absence of copper salts:, R. B. Dateer, S. Chang, J. Am. Chem. Soc. 2015, 137, 4908.
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    • For the formation of by-product 4 a, see the Supporting Information.
    • For the formation of by-product 4 a, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.