메뉴 건너뛰기




Volumn 56, Issue 6, 2017, Pages 1610-1613

A Stereoconvergent Cyclopropanation Reaction of Styrenes

Author keywords

carbenoids; catalysis; cyclopropanation; photoredox catalysis; radicals

Indexed keywords

CATALYSIS;

EID: 85008258418     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201610924     Document Type: Article
Times cited : (66)

References (63)
  • 7
    • 85010858072 scopus 로고    scopus 로고
    • Angew. Chem. 2000, 112, 4713;
    • (2000) Angew. Chem. , vol.112 , pp. 4713
  • 10
    • 85043904229 scopus 로고    scopus 로고
    • For recent related process, se
    • For recent related process, see:
  • 12
    • 85031972413 scopus 로고    scopus 로고
    • Angew. Chem. 2015, 127, 10817;
    • (2015) Angew. Chem. , vol.127 , pp. 10817
  • 14
    • 85010852230 scopus 로고    scopus 로고
    • Angew. Chem. 2016, 128, 3223;
    • (2016) Angew. Chem. , vol.128 , pp. 3223
  • 23
    • 85043915764 scopus 로고    scopus 로고
    • Kinetics of recombination for these species depends on the nature of the alkene, which affects the isomeric ratios of the cyclopropane product
    • Kinetics of recombination for these species depends on the nature of the alkene, which affects the isomeric ratios of the cyclopropane product.
  • 24
    • 85043885156 scopus 로고    scopus 로고
    • For recent examples of stereoconvergent processes with alkenes, se
    • For recent examples of stereoconvergent processes with alkenes, see:
  • 27
    • 84969156950 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 9454;
    • (2013) Angew. Chem. , vol.125 , pp. 9454
  • 29
    • 85043951874 scopus 로고    scopus 로고
    • Reactivity of radical carbenoids could be reminiscent of a carbene. Analogue metal–carbene radical species have been reporte
    • Reactivity of radical carbenoids could be reminiscent of a carbene. Analogue metal–carbene radical species have been reported:
  • 40
    • 84923260920 scopus 로고    scopus 로고
    • A redox potential difference of 0.11 V between Ru, 6 and CH, I, implies an energy barrier as low as 2.5 K cal mol, Although this electron transfer is slightly endergonic, the overall process is driven by an exergonic alkene radical addition and subsequent irreversible cyclopropane formation. For an example in photoredox catalysis involving an endergonic process, se
    • A redox potential difference of 0.11 V between RuI6 and CH2I2implies an energy barrier as low as 2.5 K cal mol−1. Although this electron transfer is slightly endergonic, the overall process is driven by an exergonic alkene radical addition and subsequent irreversible cyclopropane formation. For an example in photoredox catalysis involving an endergonic process, see: D. N. Primer, I. Karakaya, J. C. Tellis, G. A. Molander, J. Am. Chem. Soc. 2015, 137, 2195.
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 2195
    • Primer, D.N.1    Karakaya, I.2    Tellis, J.C.3    Molander, G.A.4
  • 41
    • 85099674178 scopus 로고    scopus 로고
    • Iodomethyl radical/carbocation species were invoked in UV-light-mediated stereospecific alkene cyclopropanations with CH,
    • 2:
  • 45
    • 0000451588 scopus 로고
    • Posterior DFT calculations suggested, iso, -diiodomethane (CH, =I−I) as intermediat
    • P. J. Kropp, Acc. Chem. Res. 1984, 17, 131; Posterior DFT calculations suggested iso-diiodomethane (CH2=I−I) as intermediate:
    • (1984) Acc. Chem. Res. , vol.17 , pp. 131
    • Kropp, P.J.1
  • 47
    • 85043905637 scopus 로고    scopus 로고
    • For cyclopropane synthesis involving 1,3-dihaloalkanes and radical initiators/reductants, se
    • For cyclopropane synthesis involving 1,3-dihaloalkanes and radical initiators/reductants, see:
  • 51
    • 85043859285 scopus 로고    scopus 로고
    • Preliminary results showed that the process carried out with no photocatalyst is sluggish and only 18 % yield of desired cyclopropane is observed after 18 hours
    • Preliminary results showed that the process carried out with no photocatalyst is sluggish and only 18 % yield of desired cyclopropane is observed after 18 hours.
  • 52
    • 85043911018 scopus 로고    scopus 로고
    • For stereoconvergent alkene functionalization processes in photoredox catalysis, se
    • For stereoconvergent alkene functionalization processes in photoredox catalysis, see:
  • 55
    • 84956871309 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 4059;
    • (2013) Angew. Chem. , vol.125 , pp. 4059
  • 57
    • 84981204405 scopus 로고    scopus 로고
    • Angew. Chem. 2016, 128, 2279.
    • (2016) Angew. Chem. , vol.128 , pp. 2279
  • 62
    • 17044431877 scopus 로고    scopus 로고
    • Angew. Chem. 2005, 117, 110.
    • (2005) Angew. Chem. , vol.117 , pp. 110
  • 63
    • 0004269715 scopus 로고    scopus 로고
    • (Eds., Wiley-VCH, Weinhei
    • Radicals in Organic Synthesis (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001.
    • (2001) Radicals in Organic Synthesis


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.