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Volumn 64, Issue 10, 2008, Pages 2465-2470

On the regioselectivity of the PIFA-mediated bis(trifluoroacetoxylation) of styrene-type compounds

Author keywords

Hypervalent iodine; Phenonium ions; PIFA; Styrenes

Indexed keywords

ALDEHYDE DERIVATIVE; IODINE DERIVATIVE; STYRENE DERIVATIVE; TRIFLUOROACETIC ACID;

EID: 38649126199     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.12.045     Document Type: Article
Times cited : (23)

References (64)
  • 1
    • 84891568337 scopus 로고    scopus 로고
    • Bäckvall J.-E. (Ed), Wiley-VCH, Weinheim
    • In: Bäckvall J.-E. (Ed). Modern Oxidation Methods (2004), Wiley-VCH, Weinheim
    • (2004) Modern Oxidation Methods
  • 4
    • 38649142495 scopus 로고    scopus 로고
    • See for example:
    • See for example:
  • 10
    • 38649094002 scopus 로고    scopus 로고
    • For recent reviews on the synthetic applications of polyvalent iodine reagents, see:
    • For recent reviews on the synthetic applications of polyvalent iodine reagents, see:
  • 23
    • 38649085679 scopus 로고    scopus 로고
    • For some recent contributions from our group, see:
    • For some recent contributions from our group, see:
  • 28
    • 38649140735 scopus 로고    scopus 로고
    • note
    • At higher dilution, the reaction time was prolonged excessively.
  • 29
    • 38649098821 scopus 로고    scopus 로고
    • note
    • Diesters 3a-e were identified by the aid of selective TOCSY experiments from the crude reaction prior to the addition of silica gel. See selected information in Table 1.
  • 30
    • 30744475459 scopus 로고    scopus 로고
    • The oxidation of alkenes to carbonyl compounds catalyzed by palladium(II) salts (known as the Wacker reaction) normally proceeds with Markovnikov regioselectivity. For a novel anti-Markovnikov regioselectivity (leading to aldehydes from terminal olefins) in the Wacker reaction of styrenes, see: and more recently
    • The oxidation of alkenes to carbonyl compounds catalyzed by palladium(II) salts (known as the Wacker reaction) normally proceeds with Markovnikov regioselectivity. For a novel anti-Markovnikov regioselectivity (leading to aldehydes from terminal olefins) in the Wacker reaction of styrenes, see:. Wright J.A., Gaunt M.J., and Spencer J.B. Chem.-Eur. J. 12 (2005) 949-955 and more recently
    • (2005) Chem.-Eur. J. , vol.12 , pp. 949-955
    • Wright, J.A.1    Gaunt, M.J.2    Spencer, J.B.3
  • 31
  • 32
    • 4644234793 scopus 로고    scopus 로고
    • The catalytic anti-Markovnikov hydration of terminal alkynes to aldehydes has been also described. See:
    • The catalytic anti-Markovnikov hydration of terminal alkynes to aldehydes has been also described. See:. Grotjahn D.B., and Lev D.A. J. Am. Chem. Soc. 126 (2004) 12232-12233
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 12232-12233
    • Grotjahn, D.B.1    Lev, D.A.2
  • 33
    • 21244435594 scopus 로고    scopus 로고
    • Phenylacetaldehyde (4a) is a common byproduct also obtained directly during the oxidation of styrene into styrene oxide by a number of reaction conditions. For a recent example, see:
    • Phenylacetaldehyde (4a) is a common byproduct also obtained directly during the oxidation of styrene into styrene oxide by a number of reaction conditions. For a recent example, see:. Zhang J.-L., and Che C.-M. Chem.-Eur. J. 11 (2005) 3899-3914
    • (2005) Chem.-Eur. J. , vol.11 , pp. 3899-3914
    • Zhang, J.-L.1    Che, C.-M.2
  • 34
    • 0032514970 scopus 로고    scopus 로고
    • 3 to afford the corresponding arylacetaldehydes in good yields. See:
    • 3 to afford the corresponding arylacetaldehydes in good yields. See:. Ranu B.C., and Jana U. J. Org. Chem. 63 (1998) 8212-8216
    • (1998) J. Org. Chem. , vol.63 , pp. 8212-8216
    • Ranu, B.C.1    Jana, U.2
  • 35
    • 0000614776 scopus 로고
    • Koser reported a similar alteration of the regioselectivity using HTIB. See:
    • Koser reported a similar alteration of the regioselectivity using HTIB. See:. Koser G.F. J. Org. Chem. 46 (1981) 4324-4326
    • (1981) J. Org. Chem. , vol.46 , pp. 4324-4326
    • Koser, G.F.1
  • 36
    • 13844266930 scopus 로고    scopus 로고
    • Another example of the use of hypervalent iodine reagents under solvent-free conditions can be found in:
    • Another example of the use of hypervalent iodine reagents under solvent-free conditions can be found in:. Yusubov M.S., and Wirth T. Org. Lett. 7 (2005) 519-521
    • (2005) Org. Lett. , vol.7 , pp. 519-521
    • Yusubov, M.S.1    Wirth, T.2
  • 38
    • 38649085372 scopus 로고    scopus 로고
    • note
    • It must be pointed out that a control experiment carried out with styrene 1c using PIDA [phenyliodine(III) diacetate], instead of PIFA, under the same reaction conditions resulted in the recovery of the starting material completely unchanged. This result evidences the superior activity of PIFA over PIDA.
  • 39
    • 33845553556 scopus 로고
    • For spectroscopic information of aldehyde 4b, see:
    • For spectroscopic information of aldehyde 4b, see:. Miyaura N., Maeda K., and Suginome H. J. Org. Chem. 47 (1982) 2117-2120
    • (1982) J. Org. Chem. , vol.47 , pp. 2117-2120
    • Miyaura, N.1    Maeda, K.2    Suginome, H.3
  • 40
    • 0032514970 scopus 로고    scopus 로고
    • For 4c,d, see:
    • For 4c,d, see:. Ranu B.C., and Jana U. J. Org. Chem. 63 (1998) 8212-8216
    • (1998) J. Org. Chem. , vol.63 , pp. 8212-8216
    • Ranu, B.C.1    Jana, U.2
  • 42
    • 0001613419 scopus 로고
    • 6 times higher than the triflate group in the particular reaction of a phenyliodonium salt.
    • 6 times higher than the triflate group in the particular reaction of a phenyliodonium salt. Okuyama T., Takino T., Sueda T., and Ochiai M. J. Am. Chem. Soc. 117 (1995) 3360-3367
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 3360-3367
    • Okuyama, T.1    Takino, T.2    Sueda, T.3    Ochiai, M.4
  • 43
    • 38649114102 scopus 로고    scopus 로고
    • note
    • In these cases, donating methoxy groups are placed at 2- and 4-positions, an electronic feature required to stabilize positively charged species III. Consequently, the methoxy group located at the meta position in styrene 1d disfavors the stability of intermediate III, which explains the dramatic decrease in the yield for its transformation into 4d.
  • 54
    • 38649118243 scopus 로고    scopus 로고
    • See also Ref. 9b.
    • See also Ref. 9b.
  • 55
    • 38649102859 scopus 로고    scopus 로고
    • In both cases, olefins 1h,i required 12-14 h for their complete conversion instead of the standard 3-4 h;
    • In both cases, olefins 1h,i required 12-14 h for their complete conversion instead of the standard 3-4 h;
  • 56
    • 38649138359 scopus 로고    scopus 로고
    • Aliphatic olefins behave in a similar way with PIFA to afford 1,2-bistrifluoroacetates. See Ref. 6;
    • Aliphatic olefins behave in a similar way with PIFA to afford 1,2-bistrifluoroacetates. See Ref. 6;
  • 57
    • 0038512211 scopus 로고    scopus 로고
    • 4 in methanol. For spectroscopic data of diol 6h, see:
    • 4 in methanol. For spectroscopic data of diol 6h, see:. Tanaka Y., Nishimura K., and Tomioka K. Tetrahedron 59 (2003) 4549-4556
    • (2003) Tetrahedron , vol.59 , pp. 4549-4556
    • Tanaka, Y.1    Nishimura, K.2    Tomioka, K.3
  • 60
    • 0242415168 scopus 로고    scopus 로고
    • For diol 7i, see:
    • For diol 7i, see:. Katz C.E., and Aubé J. J. Am. Chem. Soc. 125 (2003) 13948-13949
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 13948-13949
    • Katz, C.E.1    Aubé, J.2
  • 61
    • 33747391903 scopus 로고    scopus 로고
    • Carbonyl compounds 4j-l were spectroscopically identified by comparison with the reported data. For ketone 4j, see:
    • Carbonyl compounds 4j-l were spectroscopically identified by comparison with the reported data. For ketone 4j, see:. Khanh-Van Tran K.-V., and Bickar D. J. Org. Chem. 71 (2006) 6640-6643
    • (2006) J. Org. Chem. , vol.71 , pp. 6640-6643
    • Khanh-Van Tran, K.-V.1    Bickar, D.2
  • 64
    • 38649142494 scopus 로고    scopus 로고
    • note
    • At this stage, there is no clear explanation to the fact that no 1,2-addition of trifluoroacetate groups to styrene 1j is detected, as it would have been anticipated considering the lack of activation of the phenyl ring.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.