메뉴 건너뛰기




Volumn 13, Issue 12, 2011, Pages 3282-3284

Rhodium-catalyzed synthesis of germoles via the activation of carbon-germanium bonds

Author keywords

[No Author keywords available]

Indexed keywords


EID: 79958773826     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201251e     Document Type: Article
Times cited : (27)

References (33)
  • 1
    • 0002799996 scopus 로고    scopus 로고
    • For leading references on the C-Si bond cleavage in coupling reactions, see
    • For leading references on the C-Si bond cleavage in coupling reactions, see: Hiyama, T.; Shirakawa, E. Top. Curr. Chem. 2002, 219, 61
    • (2002) Top. Curr. Chem. , vol.219 , pp. 61
    • Hiyama, T.1    Shirakawa, E.2
  • 7
    • 4644245555 scopus 로고    scopus 로고
    • For a leading review on the mechanism of C-Sn bond cleavage in the Migita-Kosugi-Stille coupling reaction, see
    • For a leading review on the mechanism of C-Sn bond cleavage in the Migita-Kosugi-Stille coupling reaction, see: Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 4704
    • Espinet, P.1    Echavarren, A.M.2
  • 8
    • 0001148530 scopus 로고    scopus 로고
    • For selected catalytic reactions involving the cleavage of C-Pb bonds, see
    • For selected catalytic reactions involving the cleavage of C-Pb bonds, see: Kang, S.-K.; Choi, S.-C.; Ryu, H.-C.; Yamaguchi, T. J. Org. Chem. 1998, 63, 5748
    • (1998) J. Org. Chem. , vol.63 , pp. 5748
    • Kang, S.-K.1    Choi, S.-C.2    Ryu, H.-C.3    Yamaguchi, T.4
  • 10
    • 79958862234 scopus 로고    scopus 로고
    • For a notable exception, in which C-Si bond activation in metal silanolates has been proposed to proceed without forming pentacoordinated silicate species, see ref 1b
    • For a notable exception, in which C-Si bond activation in metal silanolates has been proposed to proceed without forming pentacoordinated silicate species, see ref 1b.
  • 13
    • 79959221584 scopus 로고    scopus 로고
    • J. Am. Chem. Soc. 2011, in press; doi: 10.1021/ja2024959
    • Liang, Y.; Zhang, S.; Xi, Z. J. Am. Chem. Soc. 2011, in press; doi: 10.1021/ja2024959.
    • Liang, Y.1    Zhang, S.2    Xi, Z.3
  • 17
    • 0346908681 scopus 로고    scopus 로고
    • 3)-Ge bonds in allylgermanium reagents can be cleaved in the presence of Lewis acids: In;, Eds.; Wiley-VCH: Weinheim
    • 3)-Ge bonds in allylgermanium reagents can be cleaved in the presence of Lewis acids: Akiyama, T. In Main Group Metals in Organic Synthesis; Yamamoto, H.; Oshima, K., Eds.; Wiley-VCH: Weinheim, 2004; pp 593-619.
    • (2004) Main Group Metals in Organic Synthesis , pp. 593-619
    • Akiyama, T.1    Yamamoto, H.2    Oshima, K.3
  • 21
    • 79958845927 scopus 로고    scopus 로고
    • DABCO serves as a base to generate a catalytically active Rh-OH species (see ref 10). The formation of hypervalent germanate species by the coordination of DABCO is unlikely under these conditions because (1) the boron atom in 1 is much more Lewis acidic to accept DABCO and (2) at least one halogen atom on the germanium center is reported to be required for the formation of pentacoordinated germanates using a fluoride activator (see ref 2c)
    • DABCO serves as a base to generate a catalytically active Rh-OH species (see ref 10). The formation of hypervalent germanate species by the coordination of DABCO is unlikely under these conditions because (1) the boron atom in 1 is much more Lewis acidic to accept DABCO and (2) at least one halogen atom on the germanium center is reported to be required for the formation of pentacoordinated germanates using a fluoride activator (see ref 2c).
  • 22
    • 0025405140 scopus 로고
    • For other catalytic synthesis of germoles, see
    • For other catalytic synthesis of germoles, see: Tsumuraya, T.; Ando, W. Organometallics 1990, 9, 869
    • (1990) Organometallics , vol.9 , pp. 869
    • Tsumuraya, T.1    Ando, W.2
  • 26
    • 79958800266 scopus 로고    scopus 로고
    • In the present study, reactions were routinely conducted at 80 °C, since several alkynes produced germoles in lower yields at room temperature
    • In the present study, reactions were routinely conducted at 80 °C, since several alkynes produced germoles in lower yields at room temperature.
  • 27
    • 79958855804 scopus 로고    scopus 로고
    • A benzyl group is expected to be cleaved more facilely if a pentacoordinate germanate intermediate is involved based on the reactivity of corresponding silanes. See refs 2b and 7b
    • A benzyl group is expected to be cleaved more facilely if a pentacoordinate germanate intermediate is involved based on the reactivity of corresponding silanes. See refs 2b and 7b.
  • 28
    • 79958855803 scopus 로고    scopus 로고
    • Electronic factors of alkynes may also affect the Me/Ph cleavage ratio
    • Electronic factors of alkynes may also affect the Me/Ph cleavage ratio.
  • 33
    • 79958805725 scopus 로고    scopus 로고
    • A preliminary study revealed that some of the benzogermoles synthesized exhibited intense photoluminescence in the solid state. See Supporting Information for details
    • A preliminary study revealed that some of the benzogermoles synthesized exhibited intense photoluminescence in the solid state. See Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.