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Volumn 128, Issue 47, 2006, Pages 15076-15077

Sequential hydrocarbon functionalization: Allylic C-H oxidation/vinylic C-H arylation

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DINITROBENZOATE; BENZOIC ACID DERIVATIVE; BORONIC ACID DERIVATIVE; CARBOXYLIC ACID; FUNCTIONAL GROUP; HYDROCARBON; ORGANOBORON DERIVATIVE; PALLADIUM; STYRENE; SULFOXIDE;

EID: 33845217953     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066563d     Document Type: Article
Times cited : (194)

References (26)
  • 12
    • 27644475970 scopus 로고    scopus 로고
    • Wiley-VCH: Weinheim. Germany
    • Hall, D. G. Boronic Acids; Wiley-VCH: Weinheim. Germany, 2005; p 14.
    • (2005) Boronic Acids , pp. 14
    • Hall, D.G.1
  • 17
    • 33845195535 scopus 로고    scopus 로고
    • note
    • AcOH is added to promote arylation when a more valuable acid is used for allylic oxidation (entries 6-11, Table 2).
  • 20
    • 0001736452 scopus 로고
    • Internal olefins with allylic acetoxy, alkoxy groups undergo regioselective anti-Markovnikov oxypalladation with Pd inserting adjacent to the allylic oxygen substituent: Tsuji, J.; Nagahima, H.; Hori, K. Tetrahedron Lett. 1982, 23, 2679.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 2679
    • Tsuji, J.1    Nagahima, H.2    Hori, K.3
  • 21
    • 33749509027 scopus 로고    scopus 로고
    • Formation of terminal olefin products is consistent with transmetalation/ insertion but not with a C-H cleavage/transmetalation mechanism: Chen, X; Goodhue, C.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634. tert-Butylethylene (lacking an allylic hydrogen) is an excellent substrate for the vinylic C-H arylation (quantitative yield, >20:1 E:Z and >20:1 internal:terminal, Supporting Information (SI)). Undecene gave a mixture of internal, terminal, benzylic olefins (4:1:1) and bisarylated products (SI).
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 12634
    • Chen, X.1    Goodhue, C.2    Yu, J.-Q.3
  • 23
    • 33845232100 scopus 로고    scopus 로고
    • note
    • 2,6-Dimethylbenzoquinone can be used in the C-H vinylation reaction, suggesting quinone does not act as a ligand (see ref 4b and SI).
  • 24
    • 33845198480 scopus 로고    scopus 로고
    • note
    • 2.
  • 25
    • 0031742384 scopus 로고    scopus 로고
    • (b) AcOH as an oxidant for Pd(0) → Pd(II)H(OAc): Trost, B.M. Chem. - Eur. J. 1998, 4, 2405.
    • (1998) Chem. - Eur. J. , vol.4 , pp. 2405
    • Trost, B.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.