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Volumn 16, Issue 31, 2010, Pages 9457-9461

Ethynyl-1,2-benziodoxol-3(1H)-one (EBX): An exceptional reagent for the ethynylation of keto, cyano, and nitro esters

Author keywords

Alkynylation; Hypervalent compounds; Iodine; Quaternary carbon atoms; Umpolung

Indexed keywords

ALKYNYLATIONS; ENOLATES; ETHYNYL; ETHYNYLATION; HIGH YIELD; HYPERVALENT COMPOUNDS; IN-SITU; MILD REACTION CONDITIONS; NITRO GROUP; NON NATURAL AMINO ACIDS; QUATERNARY CARBON ATOMS; QUATERNARY CENTERS; SELECTIVE REDUCTION; UMPOLUNG;

EID: 77955825507     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001539     Document Type: Article
Times cited : (171)

References (66)
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    • (Ed.: K. Akiba), Wiley-VCH, Weinheim, Chapter 12
    • l) M. Ochiai in Chemistry of Hypervalent Compounds (Ed.: K. Akiba), Wiley-VCH, Weinheim, 1999, Chapter 12, pp. 359-389;
    • (1999) Chemistry of Hypervalent Compounds , pp. 359-389
    • Ochiai, M.1
  • 44
    • 77949382971 scopus 로고    scopus 로고
    • and references therein
    • Angew. Chem. Int. Ed. 2010, 49, 2096, and references therein.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 2096
  • 53
    • 77955818532 scopus 로고    scopus 로고
    • [8b] only a 46% yield of 13b was obtained. The use of the phase-transfer conditions reported in Table 1, entry 3 for substrate 12c gave 13c in only 24% yield
    • [8b] only a 46% yield of 13b was obtained. The use of the phase-transfer conditions reported in Table 1, entry 3 for substrate 12c gave 13c in only 24% yield.
  • 64
    • 77955795278 scopus 로고    scopus 로고
    • In particular, an acetylene C-H signal was now visible at δ=3.50 ppm. See Figure S1 in the Supporting Information
    • In particular, an acetylene C-H signal was now visible at δ=3.50 ppm. See Figure S1 in the Supporting Information.
  • 65
    • 77955837930 scopus 로고    scopus 로고
    • In the case of slower-reacting substrates, partial decomposition of EBX was also observed
    • In the case of slower-reacting substrates, partial decomposition of EBX was also observed.
  • 66
    • 77955834307 scopus 로고    scopus 로고
    • For reasons of synthetic accessibility, the labeled TIPS-EBX reagent 18 was used. Generally, TIPS-EBX (1) was as efficient as TMS-EBX (2) as the reagent precursor, although the silyl-group removal was slightly slower
    • For reasons of synthetic accessibility, the labeled TIPS-EBX reagent 18 was used. Generally, TIPS-EBX (1) was as efficient as TMS-EBX (2) as the reagent precursor, although the silyl-group removal was slightly slower.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.