메뉴 건너뛰기




Volumn 2017, Issue 15, 2017, Pages 2122-2125

Photoredox-Catalyzed Cyclopropanation of Michael Acceptors

Author keywords

Carbenoids; Cyclization; Cyclopropane; Photocatalysis; Radicals

Indexed keywords


EID: 85013347462     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201601604     Document Type: Article
Times cited : (32)

References (73)
  • 6
    • 84930655372 scopus 로고    scopus 로고
    • Angew. Chem., 2012, 124, 8187;
    • (2012) Angew. Chem. , vol.124 , pp. 8187
  • 9
    • 85017574326 scopus 로고    scopus 로고
    • Angew. Chem., 2014, 126, 13781;
    • (2014) Angew. Chem. , vol.126 , pp. 13781
  • 12
    • 84971341754 scopus 로고    scopus 로고
    • Angew. Chem., 2015, 127, 12307;
    • (2015) Angew. Chem. , vol.127 , pp. 12307
  • 14
    • 84962952579 scopus 로고    scopus 로고
    • Angew. Chem., 2015, 127, 15058;
    • (2015) Angew. Chem. , vol.127 , pp. 15058
  • 16
    • 85017592733 scopus 로고    scopus 로고
    • Angew. Chem., 2016, 128, 3721;
    • (2016) Angew. Chem. , vol.128 , pp. 3721
  • 18
    • 85017582884 scopus 로고    scopus 로고
    • Angew. Chem., 2016, 128, 26344;
    • (2016) Angew. Chem. , vol.128 , pp. 26344
  • 25
    • 85010858072 scopus 로고    scopus 로고
    • Angew. Chem., 2000, 112, 4713;
    • (2000) Angew. Chem. , vol.112 , pp. 4713
  • 29
    • 85017573929 scopus 로고    scopus 로고
    • Angew. Chem., 2015, 127, 14314.
    • (2015) Angew. Chem. , vol.127 , pp. 14314
  • 34
    • 0000977173 scopus 로고
    • For selected examples with sulfur ylides, see a
    • For selected examples with sulfur ylides, see: a) E. J. Corey and M. Chaykovsky, J. Am. Chem. Soc., 1962, 84, 3782;
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 3782
    • Corey, E.J.1    Chaykovsky, M.2
  • 37
    • 0000799953 scopus 로고    scopus 로고
    • Angew. Chem., 2001, 113, 1482;
    • (2001) Angew. Chem. , vol.113 , pp. 1482
  • 41
    • 85017589742 scopus 로고    scopus 로고
    • Angew. Chem., 2003, 115, 852;
    • (2003) Angew. Chem. , vol.115 , pp. 852
  • 43
    • 84894520118 scopus 로고    scopus 로고
    • For recent alternative catalytic methylenation processes, see a
    • For recent alternative catalytic methylenation processes, see: a) T. Den Hartog, J. M. S. Toro and P. Chen, Org. Lett., 2014, 16, 1100;
    • (2014) Org. Lett. , vol.16 , pp. 1100
    • Den Hartog, T.1    Toro, J.M.S.2    Chen, P.3
  • 45
    • 85031972413 scopus 로고    scopus 로고
    • Angew. Chem., 2015, 127, 10817;
    • (2015) Angew. Chem. , vol.127 , pp. 10817
  • 47
    • 85010852230 scopus 로고    scopus 로고
    • Angew. Chem., 2016, 128, 3223;
    • (2016) Angew. Chem. , vol.128 , pp. 3223
  • 60
    • 85017609491 scopus 로고    scopus 로고
    • Angew. Chem., 2017, 129, 1632.
    • (2017) Angew. Chem. , vol.129 , pp. 1632
  • 61
    • 85017664981 scopus 로고    scopus 로고
    • For a description of the proposed mechanism, see ref
    • For a description of the proposed mechanism, see ref.
  • 62
    • 0000004695 scopus 로고
    • The generation of iodomethyl radical species with CH, I, /BEt, /O, and subsequent 1,4-addition to methyl vinyl ketone to give a Michael adduct, has been reporte
    • The generation of iodomethyl radical species with CH2I2/BEt3/O2 and subsequent 1,4-addition to methyl vinyl ketone to give a Michael adduct, has been reported: K. Nozaki, K. Oshima and K. Utimoto, Bull. Chem. Soc. Jpn., 1991, 64, 403.
    • (1991) Bull. Chem. Soc. Jpn. , vol.64 , pp. 403
    • Nozaki, K.1    Oshima, K.2    Utimoto, K.3
  • 63
    • 85017613190 scopus 로고    scopus 로고
    • Preliminary results showed that the process carried out with no photocatalyst is sluggish15 % NMR yield of 3a was obtained in combination with a mixture of (E), Z)-chalcone (2.21, 82 % NMR)
    • Preliminary results showed that the process carried out with no photocatalyst is sluggish, and 15 % NMR yield of 3a was obtained in combination with a mixture of (E)-/(Z)-chalcone (2.2:1, 82 % NMR).
  • 64
    • 79551693079 scopus 로고    scopus 로고
    • An experiment carried out with chalcone 1e during 30 h provided cyclopropane 3e in 22 % NMR yield. This result clearly suggests cyclopropane decomposition under the reaction conditions. We believe that an unproductive cyclopropane ring-opening could be occurring through a one-electron reduction of the carbonyl group to the corresponding radical anion. This photoredox process has been exploited by Yoon and co-workers for a [3+2] cycloaddition of aryl cyclopropyl ketone
    • An experiment carried out with chalcone 1e during 30 h provided cyclopropane 3e in 22 % NMR yield. This result clearly suggests cyclopropane decomposition under the reaction conditions. We believe that an unproductive cyclopropane ring-opening could be occurring through a one-electron reduction of the carbonyl group to the corresponding radical anion. This photoredox process has been exploited by Yoon and co-workers for a [3+2] cycloaddition of aryl cyclopropyl ketones: Z. Lu, M. Shen and T. P. Yoon, J. Am. Chem. Soc., 2011, 133, 1162.
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 1162
    • Lu, Z.1    Shen, M.2    Yoon, T.P.3
  • 65
    • 84899936504 scopus 로고    scopus 로고
    • For examples of photoredox-catalyzed Minisci-type C–H functionalization processes, see a
    • For examples of photoredox-catalyzed Minisci-type C–H functionalization processes, see: a) D. A. DiRocco, K. Dykstra, S. Krska, P. Vachal, D. V. Conway and M. Tudge, Angew. Chem. Int. Ed., 2014, 53, 4802;
    • (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 4802
    • DiRocco, D.A.1    Dykstra, K.2    Krska, S.3    Vachal, P.4    Conway, D.V.5    Tudge, M.6
  • 66
    • 84938352161 scopus 로고    scopus 로고
    • Angew. Chem., 2014, 126, 4902.
    • (2014) Angew. Chem. , vol.126 , pp. 4902
  • 68
    • 84929343497 scopus 로고    scopus 로고
    • Angew. Chem., 2015, 127, 1585;
    • (2015) Angew. Chem. , vol.127 , pp. 1585
  • 71
    • 85017572390 scopus 로고    scopus 로고
    • We observed full starting material conversion for all substrates of Table and no Michael adducts from an incomplete ring-closure event. The low yields observed for some of the cyclopropanes can also be explained as in ref
    • We observed full starting material conversion for all substrates of Table and no Michael adducts from an incomplete ring-closure event. The low yields observed for some of the cyclopropanes can also be explained as in ref.
  • 72
    • 0006170068 scopus 로고    scopus 로고
    • Corey–Chaykovsky methodologies based on sulfur ylides fail to give the cyclopropane core with enones like 4binstead the corresponding oxirane is formed. For a reference, se
    • Corey–Chaykovsky methodologies based on sulfur ylides fail to give the cyclopropane core with enones like 4b, and instead the corresponding oxirane is formed. For a reference, see: M. Lautens, M. L. Maddess, E. L. O. Sauer and S. G. Ouellet, Org. Lett., 2002, 4, 83.
    • (2002) Org. Lett. , vol.4 , pp. 83
    • Lautens, M.1    Maddess, M.L.2    Sauer, E.L.O.3    Ouellet, S.G.4
  • 73
    • 85017584842 scopus 로고    scopus 로고
    • we cannot rule out the formation of a benzyl radical intermediate in substrates bearing an aromatic ring at the β-position
    • Although our original working hypothesis was based on the formation of an α-carbonyl radical intermediate (Scheme b), we cannot rule out the formation of a benzyl radical intermediate in substrates bearing an aromatic ring at the β-position.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.