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Volumn 79, Issue 16, 2014, Pages 7277-7285

Metal-free protodeboronation of electron-rich arene boronic acids and its application to ortho -functionalization of electron-rich arenes using a boronic acid as a blocking group

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; PROTONS; SUBSTITUTION REACTIONS;

EID: 84906091508     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500780b     Document Type: Article
Times cited : (44)

References (37)
  • 2
    • 0037244546 scopus 로고    scopus 로고
    • Some heteroaromatic boronic acids are generally known to be unstable; see
    • Some heteroaromatic boronic acids are generally known to be unstable; see: Tyrrell, E.; Brookes, P. Synthesis 2003, 469-483
    • (2003) Synthesis , pp. 469-483
    • Tyrrell, E.1    Brookes, P.2
  • 6
    • 77952340967 scopus 로고    scopus 로고
    • Highly unstable heteroaromatic boronic acids, such as 2-pyridineboronic acid, are known to undergo decomposition via protodeboronation; see
    • Highly unstable heteroaromatic boronic acids, such as 2-pyridineboronic acid, are known to undergo decomposition via protodeboronation; see: Dick, G. R.; Knapp, D. M.; Gillis, E. P.; Burke, M. D. Org. Lett. 2010, 12, 2314-2317
    • (2010) Org. Lett. , vol.12 , pp. 2314-2317
    • Dick, G.R.1    Knapp, D.M.2    Gillis, E.P.3    Burke, M.D.4
  • 11
    • 84890184399 scopus 로고
    • The sulfonyl group has been used as a para -blocking group in EAS reactions; see: In, 4th ed. Wiley-VCH: New York, Chapter 11
    • The sulfonyl group has been used as a para -blocking group in EAS reactions; see: March, J. In Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-VCH: New York, 1992; Chapter 11, p 556.
    • (1992) Advanced Organic Chemistry: Reactions, Mechanisms, and Structure , pp. 556
    • March, J.1
  • 12
    • 84906079846 scopus 로고    scopus 로고
    • a values of the proton sources in Table 2 are obtained from the Evans group homepage at Harvard University; see
    • a values of the proton sources in Table 2 are obtained from the Evans group homepage at Harvard University; see: http://www2.lsdiv. harvard.edu/labs/evans/pdf/evans-pKa-table.pdf.
  • 14
    • 84855882765 scopus 로고    scopus 로고
    • The substituent effect on the protodeboronation is in good accordance with that in reactivity in electrophilic aromatic substitution. For a substituent effect on EAS reactions, see: 5th ed. Kluwer Academic/Plenum Publishers: New York, Chapter 3
    • The substituent effect on the protodeboronation is in good accordance with that in reactivity in electrophilic aromatic substitution. For a substituent effect on EAS reactions, see: Carey, F. C.; Sundberg, R. J. Advanced Organic Chemistry, Part A: Structure and Mechanisms, 5th ed.; Kluwer Academic/Plenum Publishers: New York, 2001; Chapter 3, pp 335-344.
    • (2001) Advanced Organic Chemistry, Part A: Structure and Mechanisms , pp. 335-344
    • Carey, F.C.1    Sundberg, R.J.2
  • 15
    • 70450207521 scopus 로고    scopus 로고
    • For a review on MIDA boronates, see
    • For a review on MIDA boronates, see: Gillis, E. P.; Burke, M. D. Aldrichimica Acta 2009, 42, 17-27
    • (2009) Aldrichimica Acta , vol.42 , pp. 17-27
    • Gillis, E.P.1    Burke, M.D.2
  • 27
    • 84864486737 scopus 로고    scopus 로고
    • Because 1a is more prone to undergo protodeboronation under acidic conditions, we need to carry out aromatic nitration reactions under neutral conditions. For a recent example, see
    • Because 1a is more prone to undergo protodeboronation under acidic conditions, we need to carry out aromatic nitration reactions under neutral conditions. For a recent example, see: Nowrouzi, N.; Mehranpour, A. M.; Bashiri, E.; Shayan, Z. Tetrahedron Lett. 2012, 53, 4841-4842
    • (2012) Tetrahedron Lett. , vol.53 , pp. 4841-4842
    • Nowrouzi, N.1    Mehranpour, A.M.2    Bashiri, E.3    Shayan, Z.4
  • 30
    • 80052080340 scopus 로고    scopus 로고
    • Conventionally, ortho -nitro- N, N -dialkyl aniline derivatives are prepared via nucleophilic aromatic substitution of 1-fluoro-2-nitrobenzene with dialkylamine. For a recent example, see
    • Conventionally, ortho -nitro- N, N -dialkyl aniline derivatives are prepared via nucleophilic aromatic substitution of 1-fluoro-2-nitrobenzene with dialkylamine. For a recent example, see: Ren, P.; Vechorkin, O.; Csok, Z.; Salihu, I.; Scopelliti, R.; Hu, X. Dalton Trans. 2011, 40, 8906-8911
    • (2011) Dalton Trans. , vol.40 , pp. 8906-8911
    • Ren, P.1    Vechorkin, O.2    Csok, Z.3    Salihu, I.4    Scopelliti, R.5    Hu, X.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.