메뉴 건너뛰기




Volumn 16, Issue 12, 2014, Pages 3340-3343

Rhodium-catalyzed B-H activation of 1,2-azaborines: Synthesis and characterization of BN isosteres of stilbenes

Author keywords

[No Author keywords available]

Indexed keywords

1,2 AZABORINE; 1,2-AZABORINE; BORON DERIVATIVE; HETEROCYCLIC COMPOUND; RHODIUM; STILBENE DERIVATIVE;

EID: 84903156446     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501362w     Document Type: Article
Times cited : (44)

References (53)
  • 48
    • 70349970401 scopus 로고    scopus 로고
    • Lamm, A. N.; Liu, S.-Y. Mol. Biosyst. 2009, 5, 1303-1305 See the Supporting Information for details
    • (2009) Mol. Biosyst. , vol.5 , pp. 1303-1305
    • Lamm, A.N.1    Liu, S.-Y.2
  • 49
    • 0000253638 scopus 로고
    • A possible mechanism could involve an oxidative addition of the B-H bond to Rh followed by β-migratory insertion of the Rh-B bond into the styrene substrate to generate an internal Rh-benzyl intermediate. Subsequent β-hydride elimination would produce the desired trans BN stilbene product and a Rh dihydride complex which hydrogenates a second styrene substrate to restart the catalytic cycle. This proposed mechanism is analogous with ones that have been proposed for the dehydrogenative borylation reactions of pinacol borane; see: Brown, J. M.; Lloyd-Jones, G. C. J. Am. Chem. Soc. 1994, 116, 866-878
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 866
    • Brown, J.M.1    Lloyd-Jones, G.C.2
  • 52
    • 71549116080 scopus 로고    scopus 로고
    • This observation is consistent with the larger covalent radius of boron (0.85 Å) vs carbon (0.75 Å); see: Pyykkö, P.; Atsumi, M. Chem.-Eur. J. 2009, 15, 12770-12779
    • (2009) Chem.-Eur. J. , vol.15 , pp. 12770-12779
    • Pyykkö, P.1    Atsumi, M.2
  • 53
    • 0034248485 scopus 로고    scopus 로고
    • Biradical states include singlet phantom state, triplet excited state, and triplet phantom state. Lewis, F. D.; Weigel, W. J. Phys. Chem. A 2000, 104, 8146-8153
    • (2000) J. Phys. Chem. A , vol.104 , pp. 8146-8153
    • Lewis, F.D.1    Weigel, W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.