메뉴 건너뛰기




Volumn 54, Issue 27, 2015, Pages 7872-7876

Dual Hypervalent Iodine(III) Reagents and Photoredox Catalysis Enable Decarboxylative Ynonylation under Mild Conditions

Author keywords

decarboxylation; homogeneous catalysis; hypervalent compounds; photochemistry; ynonylation

Indexed keywords

CARBOXYLATION; FUNCTIONAL GROUPS; IODINE; LIGHT; PHOTOCHEMICAL REACTIONS;

EID: 84934906497     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201502369     Document Type: Article
Times cited : (202)

References (66)
  • 2
    • 54749151096 scopus 로고    scopus 로고
    • Angew. Chem. 2008, 120, 3144-3164.
    • (2008) Angew. Chem. , vol.120 , pp. 3144-3164
  • 8
    • 84934918922 scopus 로고    scopus 로고
    • Angew. Chem. 2015, 127, 1901-1904.
    • (2015) Angew. Chem. , vol.127 , pp. 1901-1904
  • 10
    • 54749101226 scopus 로고    scopus 로고
    • Angew. Chem. 2008, 120, 3085-3088
    • (2008) Angew. Chem. , vol.120 , pp. 3085-3088
  • 12
    • 0035034185 scopus 로고    scopus 로고
    • The HIR-ketoacid complex was reported before; however, only the oxidative reactivity of HIR was demonstrated, see.
    • The HIR-ketoacid complex was reported before; however, only the oxidative reactivity of HIR was demonstrated, see, H. Togo, M. Katohgi, Synlett 2001, 565-581.
    • (2001) Synlett , pp. 565-581
    • Togo, H.1    Katohgi, M.2
  • 17
    • 84899013705 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 10632-10636.
    • (2011) Angew. Chem. , vol.123 , pp. 10632-10636
  • 18
    • 85028204287 scopus 로고    scopus 로고
    • The alternative approach is the transition-metal-catalyzed carbonylative ynonylation between organic halides and terminal alkynes at a high carbon monoxide pressure; however, the undesired Sonogashira reaction and toxic carbon monoxide limited its wide applications; see
    • The alternative approach is the transition-metal-catalyzed carbonylative ynonylation between organic halides and terminal alkynes at a high carbon monoxide pressure; however, the undesired Sonogashira reaction and toxic carbon monoxide limited its wide applications; see
  • 21
    • 84862088926 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 10978-10989.
    • (2011) Angew. Chem. , vol.123 , pp. 10978-10989
  • 23
    • 85028207409 scopus 로고    scopus 로고
    • For selected reviews on alkynyl benziodoxoles, see
    • For selected reviews on alkynyl benziodoxoles, see
  • 25
    • 84861138844 scopus 로고    scopus 로고
    • for early studies, see
    • J. P. Brand, J. Waser, Chem. Soc. Rev. 2012, 41, 4165-4179; for early studies, see
    • (2012) Chem. Soc. Rev. , vol.41 , pp. 4165-4179
    • Brand, J.P.1    Waser, J.2
  • 29
    • 77949353823 scopus 로고    scopus 로고
    • Angew. Chem. 2009, 121, 9510-9513
    • (2009) Angew. Chem. , vol.121 , pp. 9510-9513
  • 31
    • 84900446977 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 2760-2764
    • (2014) Angew. Chem. , vol.126 , pp. 2760-2764
  • 34
    • 84906879111 scopus 로고    scopus 로고
    • for selected examples on alkyl radical alkynylations, see
    • Z. Wang, L. Li, Y. Huang, J. Am. Chem. Soc. 2014, 136, 12233-12236; for selected examples on alkyl radical alkynylations, see
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 12233-12236
    • Wang, Z.1    Li, L.2    Huang, Y.3
  • 37
    • 85028200852 scopus 로고    scopus 로고
    • For reviews on acyl radicals, see
    • For reviews on acyl radicals, see
  • 42
    • 85028214974 scopus 로고    scopus 로고
    • See the Supporting Information for detailed optimizations.
    • See the Supporting Information for detailed optimizations.
  • 43
    • 0000728353 scopus 로고
    • Tertiary alkyl substituted acyl radicals decarbonylated readily to produce tertiary alkyl radicals, see.
    • Tertiary alkyl substituted acyl radicals decarbonylated readily to produce tertiary alkyl radicals, see, C. Chatgilialoglu, C. Ferreri, M. Lucarini, P. Pedrielli, G. F. Pedulli, Organometallics 1995, 14, 2672-2676.
    • (1995) Organometallics , vol.14 , pp. 2672-2676
    • Chatgilialoglu, C.1    Ferreri, C.2    Lucarini, M.3    Pedrielli, P.4    Pedulli, G.F.5
  • 47
    • 1242352716 scopus 로고
    • The dimer formation was the result of radical combinations, see.
    • The dimer formation was the result of radical combinations, see, M. J. Gibian, R. C. Corley, Chem. Rev. 1973, 73, 441-464.
    • (1973) Chem. Rev. , vol.73 , pp. 441-464
    • Gibian, M.J.1    Corley, R.C.2
  • 49
    • 49049109519 scopus 로고    scopus 로고
    • W. J. Miao, Chem. Rev. 2008, 108, 2506-2553.
    • (2008) Chem. Rev. , vol.108 , pp. 2506-2553
    • Miao, W.J.1
  • 50
    • 85028196381 scopus 로고    scopus 로고
    • The addition of BI-OAc in the dark also facilitated oxidation of the ketoacid, see Scheme S7 in the Supporting Information for the use of TEMPO as oxidants.
    • The addition of BI-OAc in the dark also facilitated oxidation of the ketoacid, see Scheme S7 in the Supporting Information for the use of TEMPO as oxidants.
  • 55
    • 84902277924 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 512-516.
    • (2014) Angew. Chem. , vol.126 , pp. 512-516
  • 61
    • 84919682122 scopus 로고    scopus 로고
    • Angew. Chem. 2009, 121, 7108.
    • (2009) Angew. Chem. , vol.121 , pp. 7108
  • 63
    • 84859785978 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 12362-12390
    • (2011) Angew. Chem. , vol.123 , pp. 12362-12390


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.