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Volumn 133, Issue 13, 2011, Pages 4668-4671

Nickel-catalyzed selective conversion of two different aldehydes to cross-coupled esters

Author keywords

[No Author keywords available]

Indexed keywords

ARYL ALDEHYDES; ATOM EFFICIENCY; CROSS-COUPLED; EQUIMOLAR MIXTURES; MECHANISTIC STUDIES;

EID: 79953859617     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja109908x     Document Type: Article
Times cited : (97)

References (46)
  • 11
    • 0035861769 scopus 로고    scopus 로고
    • Recently, catalytic hydroacylations of ketones have been reported. These are analogous to the Tishchenko reaction and give the corresponding esters with good to excellent selectivity. See
    • Recently, catalytic hydroacylations of ketones have been reported. These are analogous to the Tishchenko reaction and give the corresponding esters with good to excellent selectivity. See: Hsu, J. L.; Fang, J. M. J. Org. Chem. 2001, 66, 8573-8584
    • (2001) J. Org. Chem. , vol.66 , pp. 8573-8584
    • Hsu, J.L.1    Fang, J.M.2
  • 16
    • 79953869089 scopus 로고    scopus 로고
    • The NHCs employed in this manuscript were the following: 1,3-bis(2,6-diisopropylphenyl)-4,5-dichloroimidazol-2-ylidene (IPrCl); 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene (SIPr); 1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidene (IPr); and 1,3-bis(2,4,6-trimethylphenyl) imidazol-2-ylidene (IMes)
    • The NHCs employed in this manuscript were the following: 1,3-bis(2,6-diisopropylphenyl)-4,5-dichloroimidazol-2-ylidene (IPrCl); 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene (SIPr); 1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidene (IPr); and 1,3-bis(2,4,6-trimethylphenyl) imidazol-2-ylidene (IMes).
  • 18
    • 79953905907 scopus 로고    scopus 로고
    • For details, see the Supporting Information
    • For details, see the Supporting Information.
  • 19
    • 79953873465 scopus 로고    scopus 로고
    • 2-substituted benzaldehydes with CyCHO. However, the cross-coupled esters were not obtained at all; precipitations were observed instead, and we could not identify the products
    • 2-substituted benzaldehydes with CyCHO. However, the cross-coupled esters were not obtained at all; precipitations were observed instead, and we could not identify the products.
  • 24
    • 85121161598 scopus 로고    scopus 로고
    • For examples of a nickelacycle species proposed as a key intermediate in the nickel-catalyzed coupling reaction employing an aldehyde, see
    • For examples of a nickelacycle species proposed as a key intermediate in the nickel-catalyzed coupling reaction employing an aldehyde, see: Sato, Y.; Takanashi, T.; Mori, M. Organometallics 1999, 18, 4893
    • (1999) Organometallics , vol.18 , pp. 4893
    • Sato, Y.1    Takanashi, T.2    Mori, M.3
  • 33
    • 78649844408 scopus 로고    scopus 로고
    • For a review, see: Yuki Gosei Kagaku Kyokaishi 2009, 67, 507-516
    • Ohashi, M.; Saijo, H.; Arai, T.; Ogoshi, S. Organometallics 2010, 29, 6534-6540 For a review, see: Ogoshi, S. Yuki Gosei Kagaku Kyokaishi 2009, 67, 507-516
    • (2010) Organometallics , vol.29 , pp. 6534-6540
    • Ohashi, M.1    Saijo, H.2    Arai, T.3    Ogoshi, S.4    Ogoshi, S.5
  • 34
    • 33751553536 scopus 로고
    • For examples of an acylnickel species proposed as a key intermediate in the nickel-catalyzed coupling reaction employing an aldehyde, see
    • For examples of an acylnickel species proposed as a key intermediate in the nickel-catalyzed coupling reaction employing an aldehyde, see: Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554-2558
    • (1990) J. Org. Chem. , vol.55 , pp. 2554-2558
    • Tsuda, T.1    Kiyoi, T.2    Saegusa, T.3
  • 36
    • 37049136745 scopus 로고
    • An example of a dioxanickelacycle derived from two carbonyl compounds has been reported. See
    • An example of a dioxanickelacycle derived from two carbonyl compounds has been reported. See: Browning, J.; Green, M.; Stone, F. G. A. J. Chem. Soc. A 1971, 453-457
    • (1971) J. Chem. Soc. A , pp. 453-457
    • Browning, J.1    Green, M.2    Stone, F.G.A.3
  • 37
    • 79953839567 scopus 로고    scopus 로고
    • For an example of β-hydrogen elimination from an aldehyde moiety in the oxanickelacycle, see ref 12g
    • For an example of β-hydrogen elimination from an aldehyde moiety in the oxanickelacycle, see ref 12g.
  • 39
    • 79953876184 scopus 로고    scopus 로고
    • In ref 6, we could not conclude whether β-hydrogen elimination or reductive elimination is the rate-limiting step in the nickel-catalyzed Tishchenko reaction. However, on the basis of the results of this work, it can be assumed that reductive elimination is also the rate-limiting step of the homocoupling reaction
    • In ref 6, we could not conclude whether β-hydrogen elimination or reductive elimination is the rate-limiting step in the nickel-catalyzed Tishchenko reaction. However, on the basis of the results of this work, it can be assumed that reductive elimination is also the rate-limiting step of the homocoupling reaction.
  • 46
    • 79953887068 scopus 로고    scopus 로고
    • 8 in 53, 1, 2, and 17% yield, respectively
    • 8 in 53, 1, 2, and 17% yield, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.