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Volumn 136, Issue 44, 2014, Pages 15757-15766

Studying regioisomer formation in the pd-catalyzed fluorination of aryl triflates by deuterium labeling

Author keywords

[No Author keywords available]

Indexed keywords

ARYL TRIFLATES; DEUTERIUM LABELING; REGIOISOMERS;

EID: 84908626431     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja509144r     Document Type: Article
Times cited : (43)

References (46)
  • 33
    • 54249106704 scopus 로고    scopus 로고
    • Ortho-deprotonation of aryl chlorides and bromides by anhydrous fluoride has been previously reported. See: Grushin, V. V.; Marshall, W. J. Organometallics 2008, 27, 4825
    • (2008) Organometallics , vol.27 , pp. 4825
    • Grushin, V.V.1    Marshall, W.J.2
  • 38
    • 0038333048 scopus 로고    scopus 로고
    • Additionally, triphenylene was detected in the crude product mixture of the fluorination of phenyl triflate. Pd-catalyzed trimerization of arynes is well-known; see: Peña, D.; Escudero, S.; Pérez, D.; Guitián, E.; Castedo, L. Angew. Chem., Int. Ed. 1998, 37, 2659
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2659
    • Peña, D.1    Escudero, S.2    Pérez, D.3    Guitián, E.4    Castedo, L.5
  • 40
    • 33846452927 scopus 로고    scopus 로고
    • 3, and dppf (1,1′-bis(diphenylphosphino)ferrocene), but only a catalyst based on XantPhos provided the desired product free from biaryl byproducts, which were difficult to separate from 14. For a previous example of the use of XantPhos in Negishi couplings, see: Akao, A.; Tsuritani, T.; Kii, S.; Sato, K.; Nonoyama, N.; Mase, T.; Yasuda, N. Synlett 2007, 1, 31
    • (2007) Synlett , vol.1 , pp. 31
    • Akao, A.1    Tsuritani, T.2    Kii, S.3    Sato, K.4    Nonoyama, N.5    Mase, T.6    Yasuda, N.7
  • 42
    • 84887074433 scopus 로고    scopus 로고
    • 3/ 1, or independently prepared 9a was used as the catalyst source (Supporting Information Table S2). Additionally, reactions conducted using a catalyst derived from the more reactive di-adamantyl congener of 1, AdBrettPhos (1 ′), also show evidence of deuterium incorporation in the presence of t BuOD, with slightly lower regioselectivity and higher % aryne than those carried out with 1. For the use of 1 ′ in Pd-catalyzed fluorination, see: Lee, H. G.; Milner, P. J.; Buchwald, S. L. Org. Lett. 2013, 15, 5602
    • (2013) Org. Lett. , vol.15 , pp. 5602
    • Lee, H.G.1    Milner, P.J.2    Buchwald, S.L.3
  • 44
    • 0003277763 scopus 로고    scopus 로고
    • 19F NMR. However, the yields of these reactions are significantly lower than the standard catalytic fluorination of 3, so it is likely that t BuOD adversely affects the cross-coupling process at such high concentrations. The presence of hydrogen-bond donors can greatly affect the reactivity of Pd-F complexes; for example, see: Pilon, M. C.; Grushin, V. V. Organometallics 1998, 17, 1774
    • (1998) Organometallics , vol.17 , pp. 1774
    • Pilon, M.C.1    Grushin, V.V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.