Abstract
Various substituted N-aryl carbamoyl methyl diacetates have been synthesized from N-aryl-3-oxobutanamides via a diacetoxylation mediated by the combination of iodobenzene diacetate (PIDA)/Zn(OAc)2. This provides a new convenient method to form C–O bonds and cleave C–C bonds. Ten examples were obtained from easily available materials in good to excellent yields.
References
1.
Zhdankin V.V.
, and
Stang P.J.
, Chem. Rev. , 2008 , 108 , 5299 .
2.
Dohi T.
, and
Kita Y.
, Chem. Commun. , 2009 , 2073 .
3.
Yusubov M.S.
, and
Zhdankin V.V.
, Mendeleev Commun. , 2010 , 20 , 185 .
4.
Uyanik M.
, and
Ishihara K.
, Chem. Commun. , 2009 , 2086 .
5.
Ngatimin M.
, and
Lupton D.W.
, Aust. J. Chem. , 2010 , 63 , 653 .
6.
Yusubov M.S.
,
Nemykin V.N.
, and
Zhdankin V.V.
, Tetrahedron , 2010 , 66 , 5745 .
7.
Satam V.
,
Harad A.
,
Rajule R.
, and
Pati H.
, Tetrahedron , 2010 , 66 , 7659 .
8.
Uyanik M.
, and
Ishihara K.
, Aldrichim. Acta. , 2010 , 43 , 83 .
9.
Merritt E.A.
, and
Olofsson B.
, Angew. Chem. Int. Ed. , 2009 , 48 , 9052 .
10.
Merritt E.A.
, and
Olofsson B.
, Synthesis , 2011 , 517 .
11.
Desjardins S.
,
Andrez J.C.
, and
Canesi S.
, Org. Lett. , 2011 , 13 , 3406 .
12.
Singh F.V.
, and
Wirth T.
, Org. Lett. , 2011 , 13 , 6504 .
13.
Wang X.
,
Ye W.X.
,
Zhang S.N.
,
Feng J.J.
,
Xu Y.
,
Zhang Y.
, and
Wang J.B.
, J. Am. Chem. Soc. , 2011 , 133 , 16410 .
14.
Guilbault A.A.
, and
Legault C.Y.
, ACS Catal. , 2012 , 2 , 219 .
15.
Brand J.P.
,
González D.F.
,
Nicolai S.
, and
Waser J.
, Chem. Commun. , 2011 , 47 , 102 .
16.
Niedermann K.
,
Früh N.
,
Vinogradova E.
,
Wiehn M.S.
, and
Moreno A.
, Angew. Chem. Int. Ed. , 2011 , 50 , 1059 .
17.
Uyanik M.
,
Yasui T.
, and
Ishihara K.
, Angew. Chem. Int. Ed. , 2010 , 49 , 2175 .
18.
Liu W.B.
, and
Jiang H.F.
, Org. Lett. , 2010 , 12 , 312 .
19.
Liu W.B.
,
Chen C.
, and
Zhang Q.
, Org. Biomol. Chem. , 2011 , 9 , 4684 .
20.
Liu W.B.
,
Chen C.
,
Zhang Q.
, and
Zhu Z.B.
, Beilstein J. Org. Chem. , 2012 , 8 , 344 .
21.
Christoffers J.
, Chem. Commun. , 1997 , 943 .
22.
Biswas S.
,
Maiti S.
, and
Jana U.
, Eur. J. Org. Chem. , 2010 , 2861 .
