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Volumn 11, Issue 23, 2009, Pages 5434-5437

Stereoselective synthesis of (E)-(trisubstituted alkenyl)borinic esters: Stereochemistry reversed by ligand in the palladium-catalyzed reaction of alkynylborates with aryl halides

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; BORIC ACID; BORINIC ACID DERIVATIVE; BROMINATED HYDROCARBON; LIGAND; PALLADIUM;

EID: 72449130907     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902278q     Document Type: Article
Times cited : (53)

References (29)
  • 8
    • 0022047525 scopus 로고
    • 2 (X = halogen and thiolate) to alkynes, see: (a) Suzuki, A. Pure. Appl. Chem. 1986, 58, 629.
    • (1986) Pure. Appl. Chem. , vol.58 , pp. 629
    • Suzuki, A.1
  • 10
    • 0001017647 scopus 로고
    • For a review of the reactions of alkynyltriorganylborate with electrophiles, giving (trisubstituted alkenyl)(diorganyl)boranes, see: Negishi, E. J. Organomet. Chem. 1976, 108, 281.
    • (1976) J. Organomet. Chem. , vol.108 , pp. 281
    • Negishi, E.1
  • 14
    • 0011233632 scopus 로고
    • The protonolysis of alkenylboranes with acetic acid proceeds in a stereospecific fashion: Brown, H. C.; Zweifel, G. J. Am. Chem. Soc. 1959, 81, 1512.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 1512
    • Brown, H.C.1    Zweifel, G.2
  • 15
    • 72449162464 scopus 로고
    • For substitutive 1,2-migration from boron to the α-carbon with inversion of stereochemistry, see: Köbrich, G.; Merkle, H. R. Angew. Chem., Int. Ed. 1967, 6, 74.
    • (1967) Angew. Chem., Int. Ed. , vol.6 , pp. 74
    • Köbrich, G.1    Merkle, H.R.2
  • 16
    • 0242490677 scopus 로고    scopus 로고
    • Inversion of the stereochemistry was also observed in the palladium-catalyzed cross-coupling reaction of 2-bromo-1,3-dienes with organozinc reagents: Zeng, X.; Hu, Q.; Qian, M.; Negishi, E. J.Am. Chem. Soc. 2003, 125, 13636.
    • (2003) J.Am. Chem. Soc. , vol.125 , pp. 13636
    • Zeng, X.1    Hu, Q.2    Qian, M.3    Negishi, E.4
  • 17
    • 72449122236 scopus 로고    scopus 로고
    • An alternative mechanism is conceivable; the arylpalladium bromide A acts as an electrophile to place the palladium on the carbon, β to boron and induces migration, of a phenyl group on boron to the α-carbon. A similar mechanism has been assumed for analogous reactions of alkynylborates with alkyl halides, most of which lacked in stereoselectivity. The high stereoselectivity obtained in the present reaction led us to favor the mechanism proposed in the text
    • An alternative mechanism is conceivable; the arylpalladium bromide A acts as an electrophile to place the palladium on the carbon, β to boron and induces migration, of a phenyl group on boron to the α-carbon. A similar mechanism has been assumed for analogous reactions of alkynylborates with alkyl halides, most of which lacked in stereoselectivity. The high stereoselectivity obtained in the present reaction led us to favor the mechanism proposed in the text.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.