Abstract
A NH4I/tert-butyl hydroperoxide-promoted oxidation of tertiary N-aryl-N,N-dialkylamines in DMSO has been developed to access nitroaromatic compounds. This methodology involves sequential N-dealkylation reactions in one-pot and a radical pathway is proposed.
References
1.
Ono N.
, The nitro group in organic synthesis. Wiley , New York , 2001 .
2.
Gui J.
,
Pan C.-M.
,
Jin Y.
,
Qin T.
,
Lo J. C.
,
Lee B. J.
,
Spergel S. H.
,
Mertzman M. E.
,
Pitts W. J.
,
La Cruz T. E.
,
Schmidt M. A.
,
Darvatkar N.
,
Natarajan S. R.
, and
Baran P. S.
, Science , 2015 , 348 , 886 .
3.
Ju K.-S.
, and
Parales R. E.
, Microbiol. Mol. Biol. Rev. , 2010 , 74 , 250 .
4.
Xie F.
,
Qi Z.
, and
Li X.
, Angew. Chem., Int. Ed. , 2013 , 52 , 11862 .
5.
Liang Y.-F.
,
Li X.
,
Wang X.
,
Yan Y.
,
Feng P.
, and
Jiao N.
, ACS Catal. , 2015 , 5 , 1956 .
6.
Reitti M.
,
Villo P.
, and
Olofsson B.
, Angew. Chem., Int. Ed. , 2016 , 55 , 8928 .
7.
Fan Z.
,
Ni J.
, and
Zhang A.
, J. Am. Chem. Soc. , 2016 , 138 , 8470 .
8.
Patil V.V.
, and
Shankarling G. S.
, J. Org. Chem. , 2015 , 80 , 7876 .
9.
Reddy K.R.
,
Maheswari C. U.
,
Venkateshwar M.
, and
Kantam M. L.
, Adv. Synth. Catal. , 2009 , 351 , 93 .
10.
Chernyak N.
, and
Buchwald S. L.
, J. Am. Chem. Soc. , 2012 , 134 , 12466 .
11.
Atkins R.L.
,
Hollins R. A.
, and
Wilson W. S.
, J. Org. Chem. , 1986 , 51 , 3261 .
12.
Bäckvall J.-E.
, Selective oxidation of amines and sulfides , ed.
Bäckvall J.-E.
Wiley-VCH Verlag GmbH & Co. KGaA , Weinheim , 2010 .
13.
Ratnikov M.O.
, and
Doyle M. P.
, J. Am. Chem. Soc. , 2013 , 135 , 1549 .
14.
Li C.-J.
, Acc. Chem. Res. , 2009 , 42 , 335 .
15.
Mane R.S.
, and
Bhanage B. M.
, J. Org. Chem. , 2016 , 81 , 4974 .
16.
Zhang J.
,
Jiang J.
,
Li Y.
, and
Wan X.
J. Org. Chem. , 2013 , 78 , 11366 .
17.
Hu J.
,
Sun H.
,
Cai W.
,
Pu X.
,
Zhang Y.
, and
Shi Z.
, J. Org. Chem. , 2016 , 81 , 14 .
18.
Lida S.
, and
Toga H.
, Tetrahedron , 2007 , 63 , 8274 .
19.
Cornella J.
,
Sanchez C.
,
Banawa D.
, and
Larrosa I.
, Chem. Commun. , 2009 , 45 , 7176 .
20.
Ramanathan A.
, and
Jimenez L. S.
, Synthesis , 2010 , 217 .
21.
Lee Y.M.
,
Moon M. E.
,
Vajpayee V.
,
Filimonov V. D.
, and
Chi K.-W.
, Tetrahedron , 2010 , 66 , 7418 .
22.
Ogoshi T.
,
Takashim S.
, and
Yamagishi T.-A.
, J. Am. Chem. Soc. , 2015 , 137 , 10962 .
23.
Yoshida M.
,
Katagiri Y.
,
Zhu W.-B.
, and
Shishido K.
, Org. Biomol. Chem. , 2009 , 7 , 4062 .
24.
Emmert F.L.
,
Thomas J.
,
Hon B.
, and
Gengenbach A. J.
, Inorg. Chim. Acta , 2008 , 361 , 2243 .
25.
Xia R.
,
Xie M.-S.
,
Niu H.-Y.
,
Qu G.-R.
, and
Guo H.-M.
, Green Chem. , 2014 , 16 , 1077 .
26.
Degawa M.
, and
Hashimoto Y.
, Chem. Pharm. Bull. , 1976 , 24 , 1485 .