메뉴 건너뛰기




Volumn 12, Issue 11, 2010, Pages 2622-2625

Borostannylation of alkynes and enynes. Scope and limitations of the reaction and utility of the adducts

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIMETHYL 2 TRIMETHYLSTANNYL 2 BORA 1,3 DIAZACYCLOPENTANE; 1,3-DIMETHYL-2-TRIMETHYLSTANNYL-2-BORA-1,3-DIAZACYCLOPENTANE; ALKENE; ALKYNE; BORON DERIVATIVE; TRIMETHYLTIN;

EID: 77953011564     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100824f     Document Type: Article
Times cited : (33)

References (28)
  • 2
    • 0001594065 scopus 로고    scopus 로고
    • Palladium-catalyzed additions of 1 to alkynes including reactions that lead to carbocyclic 1,2-bisalkylidenes were initailly reported by Tanaka et al. See
    • Palladium-catalyzed additions of 1 to alkynes including reactions that lead to carbocyclic 1,2-bisalkylidenes were initailly reported by Tanaka et al. See: Onozawa, S.-y.; Hatanaka, Y.; Sakakura, T.; Shimada, S.; Tanaka, M. Organometallics 1996, 15, 5450
    • (1996) Organometallics , vol.15 , pp. 5450
    • Onozawa, S.-Y.1    Hatanaka, Y.2    Sakakura, T.3    Shimada, S.4    Tanaka, M.5
  • 6
    • 33846964661 scopus 로고    scopus 로고
    • For a review of 1,3-dimethyl-2-trimethylstannyl-2-bora-1,3- diazacyclopentane, see: Paquette, L. A., Ed.; John Wiley: New York
    • For a review of 1,3-dimethyl-2-trimethylstannyl-2-bora-1,3- diazacyclopentane, see: Tanaka, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley: New York, 2004.
    • (2004) Encyclopedia of Reagents for Organic Synthesis
    • Tanaka, M.1
  • 12
    • 0036167019 scopus 로고    scopus 로고
    • Bromoboration of an alkyne followed by reaction of the resulting dibromobora-alkene with N, N ′-dimethylethylenediamine or pinacol also gives adducts similar to 3 and 4. See
    • Bromoboration of an alkyne followed by reaction of the resulting dibromobora-alkene with N, N ′-dimethylethylenediamine or pinacol also gives adducts similar to 3 and 4. See: Lallemand, J.-Y.; Six, Y.; Ricard, L. Eur. J. Org. Chem. 2002, 503
    • (2002) Eur. J. Org. Chem. , pp. 503
    • Lallemand, J.-Y.1    Six, Y.2    Ricard, L.3
  • 14
    • 0003115131 scopus 로고    scopus 로고
    • For another reference to the formation and reactions of borostannylalkenes, see
    • For another reference to the formation and reactions of borostannylalkenes, see: Lhermitte, F.; Carboni, B. Synlett 1996, 377
    • (1996) Synlett , pp. 377
    • Lhermitte, F.1    Carboni, B.2
  • 15
    • 77952977016 scopus 로고    scopus 로고
    • See Supporting Information for experimental details and full characterization of the products
    • See Supporting Information for experimental details and full characterization of the products.
  • 16
    • 84914058906 scopus 로고
    • For examples of 2,5-azaborolidine to 2,5-oxaborolidine conversions, see
    • For examples of 2,5-azaborolidine to 2,5-oxaborolidine conversions, see: Biffar, W.; Nöth, H.; Schwerthöffer, R. Liebigs Ann. Chem. 1981, 2067
    • (1981) Liebigs Ann. Chem. , pp. 2067
    • Biffar, W.1    Nöth, H.2    Schwerthöffer, R.3
  • 19
    • 34548279222 scopus 로고    scopus 로고
    • A similar reaction using a Pd-bisphosphite catalyst has been described in the patent literature
    • A similar reaction using a Pd-bisphosphite catalyst has been described in the patent literature. Onozawa, S. y.; Tanaka, M. Jpn. Kokai Tokkyo Koho 2003, 6692
    • (2003) Jpn. Kokai Tokkyo Koho , pp. 6692
    • Onozawa, S.Y.1    Tanaka, M.2
  • 20
    • 3042793632 scopus 로고    scopus 로고
    • However, experimental and characterization details are not readily available. Trimethylsilyltributylstannane undergoes the expected Pd-catalyzed 1,2- syn -addition to acetylene. See:
    • However, experimental and characterization details are not readily available. Trimethylsilyltributylstannane undergoes the expected Pd-catalyzed 1,2- syn -addition to acetylene. See: Murakami, M.; Matsuda, T.; Itami, K.; Ashida, S.; Terayama, M. Synthesis 2004, 1522
    • (2004) Synthesis , pp. 1522
    • Murakami, M.1    Matsuda, T.2    Itami, K.3    Ashida, S.4    Terayama, M.5
  • 26
    • 0037416925 scopus 로고    scopus 로고
    • See also ref 4 a. A recent review of the chemistry of boron and silicon-substituted dienes
    • Gao, X.; Hall, D. G. Tetrahedron Lett. 2003, 44, 2231 See also ref 4 a. A recent review of the chemistry of boron and silicon-substituted dienes
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2231
    • Gao, X.1    Hall, D.G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.