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Volumn 126, Issue 28, 2004, Pages 8755-8759

Development of a catalytic electron transfer system mediated by transition metal ate complexes: Applicability and tunability of electron-releasing potential for organic transformations

Author keywords

[No Author keywords available]

Indexed keywords

CHEMOSELECTIVE CLEAVAGES; ELECTRON TRANSFER (ET);

EID: 3242722926     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039674a     Document Type: Article
Times cited : (66)

References (40)
  • 1
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    • Trost, B. M., Ed.; Pergamon Press: Oxford, Chapter 2.7 and references therein
    • Review: Brettle, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 2.7 and references therein.
    • (1991) Comprehensive Organic Synthesis , vol.3
    • Brettle, R.1
  • 13
    • 33748217152 scopus 로고    scopus 로고
    • and references therein
    • For reviews, see: (a) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 386-403 and references therein.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 386-403
    • Kauffmann, T.1
  • 15
    • 0021096063 scopus 로고
    • The absorptions of these ketyl species are consistent with the values previously reported; see: (a) Pons, S.; Davidson, T.; Bewick, A. J. Am. Chem. Soc. 1983, 105, 1802-1805.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 1802-1805
    • Pons, S.1    Davidson, T.2    Bewick, A.3
  • 18
    • 0029119899 scopus 로고
    • Recently, the potential of the sulfonamide functionality as a protective group has been suggested, as exemplified by Fukuyama's (di) nitrophenylsulfonamide protecting group, which undergoes facile cleavage under basic conditions. (a) Fukuyama, T.; Jow, C.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373-6374.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6373-6374
    • Fukuyama, T.1    Jow, C.2    Cheung, M.3
  • 21
    • 0000436886 scopus 로고
    • The reductive deprotection of the N-sulfonyl moiety is also known to proceed via a ET process from alkali metals: (a) Heathcock, C. H.; Smith, K. M.; Blumenkopf, A. B. J. Am. Chem. Soc. 1986, 108, 5022-5024.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 5022-5024
    • Heathcock, C.H.1    Smith, K.M.2    Blumenkopf, A.B.3
  • 25
    • 0000315403 scopus 로고
    • Low-valent lanthanides: (e) Vedejs, E. J. Org. Chem. 1994, 59, 1602-1603.
    • (1994) J. Org. Chem. , vol.59 , pp. 1602-1603
    • Vedejs, E.1
  • 26
    • 3242687435 scopus 로고    scopus 로고
    • note
    • Commercially available Mg turnings were used.
  • 28
    • 0000891348 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: Oxford, Chapter 2.3 and references therein
    • Review: Knight, D. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 2.3 and references therein.
    • (1991) Comprehensive Organic Synthesis , vol.3
    • Knight, D.W.1
  • 32
    • 3242671038 scopus 로고    scopus 로고
    • note
    • 3MnLi selectively gave 4-allyloxyphenol. These results clearly indicate that the present catalytic ET reactions can be controlled by the choice of ET ate complex (mediator), not by Mg (Figure 2).
  • 33
    • 3242703592 scopus 로고    scopus 로고
    • note
    • 3Mn(II)Li, the reactions were uncontrolled.
  • 34
    • 0001605152 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: Oxford, Chapter 2.6
    • For a review on the pinacol coupling reactions, see: Robertson, G. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 2.6.
    • (1991) Comprehensive Organic Synthesis , vol.3
    • Robertson, G.M.1
  • 35
    • 3242737007 scopus 로고    scopus 로고
    • note
    • The alkoxide ligated Mn(II)-ates, Co(II)-ates, and Fe(II)-ate are little known; see ref 6a.
  • 36
    • 0029842464 scopus 로고    scopus 로고
    • In recent publications, we revealed that tetracoordinated dianion-type zincates have a higher transference aptitude for ligands than tricoordinated monoanion-type zincates; see: (a) Uchiyama, M.; Koike, M.; Kameda, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1996, 118, 8733-8734.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 8733-8734
    • Uchiyama, M.1    Koike, M.2    Kameda, M.3    Kondo, Y.4    Sakamoto, T.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.