메뉴 건너뛰기




Volumn 21, Issue 28, 2015, Pages 10014-10018

Iodine(III)-Mediated para-Selective Direct Imidation of Anilides

Author keywords

C N bond formation; hypervalent iodine; oxidative coupling; para phenylenediamines; umpolung

Indexed keywords

ACETANILID; CATALYSIS; FUNCTIONAL GROUPS; NITROGEN; REGIOSELECTIVITY;

EID: 84933530927     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201501553     Document Type: Article
Times cited : (24)

References (114)
  • 1
    • 84933578560 scopus 로고    scopus 로고
    • For recent reviews on arene C-H bond amination, see
    • For recent reviews on arene C-H bond amination, see
  • 5
    • 84933578561 scopus 로고    scopus 로고
    • For general recent reviews on arene amination, see
    • For general recent reviews on arene amination, see
  • 9
    • 84933578562 scopus 로고    scopus 로고
    • in (Eds.: A. deMeijere, S. Bräse, M. Oestreich), Wiley-VCH, Weinheim, .
    • J. Paradies, in Metal-Catalyzed Cross-Coupling Reactions and More (Eds.:, A. de Meijere, S. Bräse, M. Oestreich,), Wiley-VCH, Weinheim, 2013, pp. 995-1066.
    • (2013) Metal-Catalyzed Cross-Coupling Reactions and More , pp. 995-1066
    • Paradies, J.1
  • 11
    • 84933578563 scopus 로고    scopus 로고
    • For recent reviews on ortho-directed transition-metal-catalyzed arene C-H bond functionalization, see
    • For recent reviews on ortho-directed transition-metal-catalyzed arene C-H bond functionalization, see
  • 14
    • 84893866860 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 11942-11959
    • (2013) Angew. Chem. , vol.125 , pp. 11942-11959
  • 18
    • 84933578564 scopus 로고    scopus 로고
    • For examples of intermolecular ortho-directed transition-metal-catalyzed arene C-H bond amination, see: with Pd
    • For examples of intermolecular ortho-directed transition-metal-catalyzed arene C-H bond amination, see: with Pd
  • 24
    • 84945448272 scopus 로고    scopus 로고
    • with Cu
    • Angew. Chem. 2015, 127, 2527-2530; with Cu
    • (2015) Angew. Chem. , vol.127 , pp. 2527-2530
  • 27
    • 84883003242 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 6159-6162
    • (2013) Angew. Chem. , vol.125 , pp. 6159-6162
  • 37
    • 84933578566 scopus 로고    scopus 로고
    • For examples of intermolecular radical-mediated arene amination, see
    • For examples of intermolecular radical-mediated arene amination, see
  • 50
    • 84933578567 scopus 로고    scopus 로고
    • For reviews on hypervalent iodine chemistry, see
    • For reviews on hypervalent iodine chemistry, see
  • 54
    • 84933578568 scopus 로고    scopus 로고
    • For examples of intramolecular iodine(III)-mediated arene amination, see
    • For examples of intramolecular iodine(III)-mediated arene amination, see
  • 58
    • 82455190999 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 8764-8767.
    • (2011) Angew. Chem. , vol.123 , pp. 8764-8767
  • 59
    • 84933578569 scopus 로고    scopus 로고
    • For examples of intermolecular iodine(III)-mediated arene amination, see
    • For examples of intermolecular iodine(III)-mediated arene amination, see
  • 65
    • 84933578570 scopus 로고    scopus 로고
    • For examples of arene para-functionalization, see
    • For examples of arene para-functionalization, see
  • 67
    • 84856361265 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 478-482
    • (2011) Angew. Chem. , vol.123 , pp. 478-482
  • 71
    • 84897619846 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 7387-7390
    • (2012) Angew. Chem. , vol.124 , pp. 7387-7390
  • 75
    • 84933578571 scopus 로고    scopus 로고
    • For examples of iodine(III)-mediated, nucleophilic arene para-functionalization, see
    • For examples of iodine(III)-mediated, nucleophilic arene para-functionalization, see
  • 87
    • 84880792333 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 1363-1367.
    • (2013) Angew. Chem. , vol.125 , pp. 1363-1367
  • 89
    • 84933578572 scopus 로고    scopus 로고
    • For rare examples where the triflimide anion was proposed to act as a nucleophile, see
    • For rare examples where the triflimide anion was proposed to act as a nucleophile, see
  • 92
    • 33751158510 scopus 로고
    • AgNTf2 is 25 to 35 times more expensive than LiNTf2 (calculations made from three different common suppliers, per mol of reagent). It can however be prepared at lower cost from HNTf2 and Ag2CO3, see.
    • AgNTf2 is 25 to 35 times more expensive than LiNTf2 (calculations made from three different common suppliers, per mol of reagent). It can however be prepared at lower cost from HNTf2 and Ag2CO3, see:, A. Vij, Y. Y. Zheng, R. L. Kirchmeier, J. M. Shreeve, Inorg. Chem. 1994, 33, 3281-3288.
    • (1994) Inorg. Chem. , vol.33 , pp. 3281-3288
    • Vij, A.1    Zheng, Y.Y.2    Kirchmeier, R.L.3    Shreeve, J.M.4
  • 93
    • 84933578573 scopus 로고    scopus 로고
    • We found that even with a relaxation delay set to 10 s for all quantitative NMR experiments, isolated yields were typically 5-15% higher than those calculated from the crude reaction mixture.
    • We found that even with a relaxation delay set to 10 s for all quantitative NMR experiments, isolated yields were typically 5-15% higher than those calculated from the crude reaction mixture.
  • 94
    • 84933578574 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.
  • 97
    • 33746293799 scopus 로고    scopus 로고
    • Angew. Chem. 2005, 117, 6349-6352
    • (2005) Angew. Chem. , vol.117 , pp. 6349-6352
  • 99
    • 84933578575 scopus 로고    scopus 로고
    • For reviews on the use of hypervalent iodine reagents as catalysts, see
    • For reviews on the use of hypervalent iodine reagents as catalysts, see
  • 104
    • 84933578576 scopus 로고    scopus 로고
    • In our hands, aryl triflimides 2 were found to be bench stable and could be purified by standard silica gel chromatography.
    • In our hands, aryl triflimides 2 were found to be bench stable and could be purified by standard silica gel chromatography.
  • 105
    • 84933578577 scopus 로고    scopus 로고
    • Attempts at obtaining suitable crystals of A for X-ray analysis were unsuccessful. Similar species have however been well studied and fully characterized; for examples, see
    • Attempts at obtaining suitable crystals of A for X-ray analysis were unsuccessful. Similar species have however been well studied and fully characterized; for examples, see
  • 109
    • 84933578578 scopus 로고    scopus 로고
    • No precipitation due to the formation LiOAc was observed and only one acetate signal was observed in the NMR spectra.
    • No precipitation due to the formation LiOAc was observed and only one acetate signal was observed in the NMR spectra.
  • 111
    • 55049136075 scopus 로고    scopus 로고
    • Angew. Chem. 2008, 120, 3847-3850.
    • (2008) Angew. Chem. , vol.120 , pp. 3847-3850
  • 112
    • 51549121525 scopus 로고    scopus 로고
    • For a traditional method to prepare aryl triflamides, see.
    • For a traditional method to prepare aryl triflamides, see:, A. Greenfield, C. Grosanu, Tetrahedron Lett. 2008, 49, 6300-6303.
    • (2008) Tetrahedron Lett , vol.49 , pp. 6300-6303
    • Greenfield, A.1    Grosanu, C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.