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Volumn 133, Issue 22, 2011, Pages 8478-8481

Nickel-catalyzed Kumada cross-coupling reactions of tertiary alkylmagnesium halides and aryl bromides/triflates

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDES; ARYL TRIFLATES; CROSS-COUPLINGS; ELECTROPHILES; KUMADA CROSS-COUPLING; VINYL BROMIDES; VINYL CHLORIDES;

EID: 79957979491     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja202769t     Document Type: Article
Times cited : (153)

References (36)
  • 15
    • 71549116081 scopus 로고    scopus 로고
    • While a Ni(0)-Ni(II) catalytic cycle cannot be conclusively ruled out, we favor a Ni(I)-Ni(III) catalytic cycle for such Ni-catalyzed reactions. See
    • While a Ni(0)-Ni(II) catalytic cycle cannot be conclusively ruled out, we favor a Ni(I)-Ni(III) catalytic cycle for such Ni-catalyzed reactions. See: Phapale, V. B.; Guisan-Ceinos, M.; Bunuel, E.; Cardenas, D. J. Chem.-Eur. J. 2009, 15, 12681
    • (2009) Chem.-Eur. J. , vol.15 , pp. 12681
    • Phapale, V.B.1    Guisan-Ceinos, M.2    Bunuel, E.3    Cardenas, D.J.4
  • 20
    • 34250863375 scopus 로고    scopus 로고
    • For a Cu-catalyzed cross-coupling reaction involving t -BuMgCl and primary alkyl halides, see
    • For a Cu-catalyzed cross-coupling reaction involving t -BuMgCl and primary alkyl halides, see: Terao, J.; Todo, H.; Begum, S. A.; Kuniyasu, H.; Kambe, N. Angew. Chem., Int. Ed. 2007, 46, 2086
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 2086
    • Terao, J.1    Todo, H.2    Begum, S.A.3    Kuniyasu, H.4    Kambe, N.5
  • 21
    • 79957990572 scopus 로고    scopus 로고
    • While this paper was under review, a separate Ni/NHC-catalyzed process for the cross-coupling of tertiary alkylmagnesium halides and aryl bromides was published:, not supplied.
    • Lohre, C.; Droge, T.; Wang, C.; Glorius, F. While this paper was under review, a separate Ni/NHC-catalyzed process for the cross-coupling of tertiary alkylmagnesium halides and aryl bromides was published: Chem.-Eur. J. 2011, not supplied.
    • (2011) Chem.-Eur. J.
    • Lohre, C.1    Droge, T.2    Wang, C.3    Glorius, F.4
  • 23
    • 57549115030 scopus 로고    scopus 로고
    • For reviews of NHC ligands in cross-coupling reactions, see
    • For reviews of NHC ligands in cross-coupling reactions, see: Marion, N.; Nolan, S. Acc. Chem. Res. 2008, 41, 1440
    • (2008) Acc. Chem. Res. , vol.41 , pp. 1440
    • Marion, N.1    Nolan, S.2
  • 27
    • 34250821753 scopus 로고    scopus 로고
    • While the exact role of water in this system remains unclear, there is precedent for a similarly important water effect with Ni-catalyzed Hiyama cross-coupling reactions in:;;, Additionally, the importance of water in the activation of Pd(II) salts has been previously demonstrated. See:;; Chem. Lett. 1992, 2177
    • While the exact role of water in this system remains unclear, there is precedent for a similarly important water effect with Ni-catalyzed Hiyama cross-coupling reactions in: Strotman, N. A.; Sommer, S.; Fu, G. C. Angew. Chem., Int. Ed. 2007, 46, 3556 Additionally, the importance of water in the activation of Pd(II) salts has been previously demonstrated. See: Ozawa, F.; Kubo, A.; Hayaski, T. Chem. Lett. 1992, 2177
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 3556
    • Strotman, N.A.1    Sommer, S.2    Fu, G.C.3    Ozawa, F.4    Kubo, A.5    Hayaski, T.6
  • 31
    • 79957997801 scopus 로고    scopus 로고
    • 6 with a mortar and pestle and heating the powder under high vacuum in an oil bath at 100 °C for 20 min, then at 120 °C for an additional 5-10 min (see Supporting Information for more details). The powder was rapidly stirred to ensure homogeneous heating. The extent of dehydration can be readily determined by the mass change before/after heating under vacuum.
    • 6 with a mortar and pestle and heating the powder under high vacuum in an oil bath at 100 °C for 20 min, then at 120 °C for an additional 5-10 min (see Supporting Information for more details). The powder was rapidly stirred to ensure homogeneous heating. The extent of dehydration can be readily determined by the mass change before/after heating under vacuum.
  • 32
    • 79958014933 scopus 로고    scopus 로고
    • In contrast to our original report on the Ni-catalyzed Negishi cross-coupling of secondary alkylzinc halides and aryl iodides with terpyridine as the ligand (ref 3k), the addition of LiCl (1 equiv) does not inhibit catalytic turnover or promote isomerization of the nucleophile.
    • In contrast to our original report on the Ni-catalyzed Negishi cross-coupling of secondary alkylzinc halides and aryl iodides with terpyridine as the ligand (ref 3k), the addition of LiCl (1 equiv) does not inhibit catalytic turnover or promote isomerization of the nucleophile.
  • 33
    • 79957971597 scopus 로고    scopus 로고
    • The failure of NaO t -Bu to facilitate the reaction suggests that kinetically slow in situ deprotonation of the NHC by the Grignard reagent is not responsible for the failure of the anhydrous reactions.
    • The failure of NaO t -Bu to facilitate the reaction suggests that kinetically slow in situ deprotonation of the NHC by the Grignard reagent is not responsible for the failure of the anhydrous reactions.
  • 34
    • 79958007872 scopus 로고    scopus 로고
    • Use of the vinyl bromide resulted in the formation of more reduction product than with use of the vinyl chloride.
    • Use of the vinyl bromide resulted in the formation of more reduction product than with use of the vinyl chloride.
  • 35
    • 0001547002 scopus 로고
    • Examples of the Ni-catalyzed cross-coupling of trans -β-bromostyrene and t -BuMgCl have been previously reported in
    • Examples of the Ni-catalyzed cross-coupling of trans -β-bromostyrene and t -BuMgCl have been previously reported in: Hayashi, T.; Konishi, M.; Yokota, K.; Kumada, M. Chem. Lett. 1980, 767
    • (1980) Chem. Lett. , pp. 767
    • Hayashi, T.1    Konishi, M.2    Yokota, K.3    Kumada, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.