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Volumn 52, Issue 16, 2013, Pages 4431-4434

Palladium-catalyzed ortho-selective C-H borylation of 2-phenylpyridine and its derivatives at room temperature

Author keywords

borylation; Lewis acid; Lewis base; palladium; regioselectivity

Indexed keywords

2-PHENYLPYRIDINE; BORYLATION; LEWIS ACID; LEWIS ACID-BASE INTERACTION; LEWIS BASE; PALLADIUM CATALYST; PALLADIUM-CATALYZED; ROOM TEMPERATURE;

EID: 84876221222     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201210328     Document Type: Article
Times cited : (82)

References (42)
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    • Angew. Chem. Int. Ed. 2002, 41, 3056. For recent reviews, see
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    • These data can be obtained free of charge from The Cambridge Crystallographic Data Centre. For details, see the Supporting Information
    • CCDC 926839 (3 a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif. For details, see the Supporting Information.
    • CCDC 926839 (3 A) Contains the Supplementary Crystallographic Data for This Paper
  • 33
    • 0001207310 scopus 로고
    • 11B NMR chemical shift of a mixture of 1 a and 2 a (0.3 ppm), which is similar to that of product 3 a (3.4 ppm).
    • (1985) Inorg. Chem. , vol.24 , pp. 2532
    • Narula, C.K.1    Nöth, H.2
  • 40
    • 84867356243 scopus 로고    scopus 로고
    • 11B NMR signal of a mixture of pyridine and 9-BBN was observed at 1.4 ppm. In contrast, a signal was observed at 5.7 ppm in the measurement of a mixture of pyridine, 9-BBN, and palladium catalyst. These results show that another species was formed upon addition of the palladium catalyst, one with a chemical shift suitable for a metal-boron-nitrogen species (see:, A. Zech, M. F. Haddow, H. Othman, G. R. Owen, Organometallics 2012, 31, 6753). Therefore, it can be suggested that Lewis acid-base interaction between nitrogen and boron atoms remains after Step a 2.
    • (2012) Organometallics , vol.31 , pp. 6753
    • Zech, A.1    Haddow, M.F.2    Othman, H.3    Owen, G.R.4
  • 42
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    • The palladium-catalyzed cross-coupling reaction between the borylated product 3 a and 1-iodododecane did not proceed; see:, T. Ishiyama, S. Abe, N. Miyaura, A. Suzuki, Chem. Lett. 1992, 691).
    • (1992) Chem. Lett. , pp. 691
    • Ishiyama, T.1    Abe, S.2    Miyaura, N.3    Suzuki, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.