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Volumn 72, Issue 19, 2007, Pages 7253-7259

Use of deuterium labeling studies to determine the stereochemical outcome of palladium migrations during an asymmetric intermolecular Heck reaction

Author keywords

[No Author keywords available]

Indexed keywords

INTERMOLECULAR HECK REACTION; PHENYL TRIFLATE;

EID: 34548774476     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071119u     Document Type: Article
Times cited : (36)

References (44)
  • 28
    • 34548740226 scopus 로고    scopus 로고
    • 2H NMR integration, compound 18 was 95.5% deuterated when used in further Heck reactions.
    • 2H NMR integration, compound 18 was 95.5% deuterated when used in further Heck reactions.
  • 32
    • 34548762509 scopus 로고    scopus 로고
    • 2-Phenyl-2,3-dihydrofuran (6a, 1H NMR (CDCl 3, 300 MHz) δ 7.5-7.3 (5H, m, Ph, 6.5 (1H, q, J, 2.39 Hz, H5, 5.6 (1H, dd, J, 10.76, 8.21 Hz, H2, 5.0 (1H, q, J, 2.57 Hz, H4, 3.1 (1H, ddt, J, 14.87, 10.76, 2.31 Hz, H3β, 2.7 1H, ddt, J, 15.12, 8.46, 2.31 Hz, H3α, The assignment of H3β and H 3α was done by NOE measurements. Irradiation of H2 in 6a resulted in an enhancement of the signal at 3.1 ppm while the signal at 2.7 ppm was unchanged
    • 2 in 6a resulted in an enhancement of the signal at 3.1 ppm while the signal at 2.7 ppm was unchanged,
  • 33
    • 34548752858 scopus 로고    scopus 로고
    • 1H NMR spectrum of 6b.
    • 1H NMR spectrum of 6b.
  • 34
    • 34548768764 scopus 로고    scopus 로고
    • 1H NMR spectrum of 6c.
    • 1H NMR spectrum of 6c.
  • 35
    • 34548749825 scopus 로고    scopus 로고
    • 1H NMR spectrum of 6d.
    • 1H NMR spectrum of 6d.
  • 36
    • 34548771788 scopus 로고    scopus 로고
    • 1H NMR spectrum of 6e.
    • 1H NMR spectrum of 6e.
  • 37
    • 34548778691 scopus 로고    scopus 로고
    • 5).
    • 5).
  • 38
    • 34548750974 scopus 로고    scopus 로고
    • 1H NMR spectrum of 7b.
    • 1H NMR spectrum of 7b.
  • 39
    • 34548742300 scopus 로고    scopus 로고
    • 1H NMR spectrum of 7c.
    • 1H NMR spectrum of 7c.
  • 40
    • 34548756165 scopus 로고    scopus 로고
    • 1H NMR spectrum of 7d.
    • 1H NMR spectrum of 7d.
  • 41
    • 34548795386 scopus 로고    scopus 로고
    • 1H NMR spectrum of 7e.
    • 1H NMR spectrum of 7e.
  • 42
    • 33846521293 scopus 로고    scopus 로고
    • For examples of C(sp3)-H functionalizations involving Pd, see: (a) Hitce, J, Retailleau, P, Baudoin, O. Chem.-Eur. J. 2007, 13, 792-799
    • 3)-H functionalizations involving Pd, see: (a) Hitce, J.; Retailleau, P.; Baudoin, O. Chem.-Eur. J. 2007, 13, 792-799.
  • 44
    • 33644905281 scopus 로고    scopus 로고
    • 2)-H functionalizations, see: (c) Campeau, L.-C.; Fagnou, K. Chem. Commun. 2006, 1253-1264 and references therein.
    • 2)-H functionalizations, see: (c) Campeau, L.-C.; Fagnou, K. Chem. Commun. 2006, 1253-1264 and references therein.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.