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Volumn 49, Issue 19, 2010, Pages 3334-3337

Unusual ipso substitution of diaryliodonium bromides initiated by a single-electron-transfer oxidizing process

Author keywords

C c coupling; Chemoselectivity; Electron transfer; Hypervalent compounds; Iodine

Indexed keywords

AROMATIC CATIONS; AROMATIC NUCLEOPHILES; AROMATIC SUBSTITUTIONS; BIARYLS; C-C COUPLING; CHEMICAL EQUATIONS; CHEMO-SELECTIVITY; ELECTRON TRANSFER; GOOD YIELD; HEXAFLUOROISOPROPANOL; HYPERVALENT COMPOUNDS; OXIDIZING PROCESS; SINGLE ELECTRON;

EID: 77951673295     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200907281     Document Type: Short Survey
Times cited : (184)

References (38)
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    • By exploting this principle, α-thienyl groups have been utilized successfully as nonparticipating aryl groups in ligand coupling processes of diaryliodonium salts, see : a
    • By exploting this principle, α-thienyl groups have been utilized successfully as nonparticipating aryl groups in ligand coupling processes of diaryliodonium salts, see : a) T L. Ross, J. Ermert, C. Hocke, H.H. Coenen, J. Am. Chem. Soc. 2007, 129, 8018;
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    • Symmetrical heteroaromatic salts were used to avoid this chemoselectivity issue, see: a
    • Symmetrical heteroaromatic salts were used to avoid this chemoselectivity issue, see: a) V. K. Aggarwal, B. Olofsson, Angew. Chem. 2005, 117, 5652;
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    • Aggarwal, V.K.1    Olofsson, B.2
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    • 77951670489 scopus 로고    scopus 로고
    • 3, and they gave poor results (0-28% yield of 3aa).
    • 3, and they gave poor results (0-28% yield of 3aa).
  • 29
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    • No general method dealing with selective heteroaryl transfer has yet appeared in metal-catalyzed C-H bond arylation, see Ref. [2d].
    • No general method dealing with selective heteroaryl transfer has yet appeared in metal-catalyzed C-H bond arylation, see Ref. [2d].
  • 34
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    • The cationic radical species of 2 a was also detected by ESR and UV/Vis spectroscopic measurements. See the Supporting Infor-mation.
    • The cationic radical species of 2 a was also detected by ESR and UV/Vis spectroscopic measurements. See the Supporting Infor-mation.
  • 35
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    • A few examples of carbon-based groups involved in ligand transfer from iodine(III) atoms toward aromatic cation radicals have been reported, see : a
    • A few examples of carbon-based groups involved in ligand transfer from iodine(III) atoms toward aromatic cation radicals have been reported, see : a) T. Dohi, K. Morimoto, N. Takenaga, A. Goto, A. Maruyama, Y. Kiyono, H. Tohma, Y. Kita, J. Org. Chem. 2007, 72, 109;
    • (2007) J. Org. Chem. , vol.72 , pp. 109
    • Dohi, T.1    Morimoto, K.2    Takenaga, N.3    Goto, A.4    Maruyama, A.5    Kiyono, Y.6    Tohma, H.7    Kita, Y.8
  • 37
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    • Mesitylene (2i) was less reactive in SET oxidations, see
    • Mesitylene (2i) was less reactive in SET oxidations, see: T. Dohi, M. Ito, K. Morimoto, M. Iwata, Y. Kita, Angew. Chem. 2008, 120, 1321;
    • (2008) Angew. Chem. , vol.120 , pp. 1321
    • Dohi, T.1    Ito, M.2    Morimoto, K.3    Iwata, M.4    Kita, Y.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.