Abstract
Heterogeneous double hydroamination of 2-alkynylanilines with terminal alkynes was achieved by using a magnetic nanoparticles-supported gold(III)-2,2′-bipyridine complex and silver trifluoromethanesulfonate as catalysts to afford the corresponding N-vinylindoles in moderate to good yields under mild and solvent-free conditions. The heterogeneous gold catalyst can easily be separated from the reaction mixture by simply applying an external magnet and can be recycled up to seven times without significant loss of activity.
Keywords
References
1.
Sundberg R.J.
, Indoles. Academic Press , London , 1996 .
2.
Gribble G.W.
, J. Chem. Soc., Perkin Trans. 1 , 2000 , 1045 .
3.
Faulkner D.J.
, Nat. Prod. Rep. , 1999 , 16 , 155 .
4.
Humphrey G.R.
, and
Kuethe J.T.
, Chem. Rev. , 2006 , 106 , 2875 .
5.
Shiri M.
, Chem. Rev. , 2012 , 112 , 3508 .
6.
Ogata M.
,
Matsumoto H.
,
Shimizu S.
,
Kida S.
,
Shiro M.
, and
Tawara K.
, J. Med. Chem. , 1987 , 30 , 1348 .
7.
Schultz A.G.
,
Malachowski W.P.
, and
Pan Y.
, J. Org. Chem. , 1997 , 62 , 1223 .
8.
Li H.
,
Boonnak N.
, and
Padwa A.
, J. Org. Chem. , 2011 , 76 , 9488 .
9.
Brustolin F.
,
Castelvetro V.
,
Ciardelli F.
,
Ruggeri G.
, and
Colligiani A.
, J. Polym. Sci., A: Polym. Chem. , 2001 , 39 , 253 .
10.
Priola A.
,
Gatti G.
, and
Cesca S.
, Makromol. Chem. , 1979 , 180 , 1 .
11.
Gipstein E.
, and
Hewett W.A.
, Macromolecules , 1969 , 2 , 82 .
12.
Maki Y.
,
Mori H.
, and
Endo T.
, Macromolecules , 2007 , 40 , 6119 .
13.
Artyom Y.
,
Lebedev V.V.I.
,
Denis N.
,
Beletskaya I.P.
, and
Voskoboynikov A.Z.
, Org. Lett. , 2002 , 4 , 623 .
14.
Liao Q.
,
Wang Y.
,
Zhang L.
, and
Xi C.
, J. Org. Chem. , 2009 , 74 , 6371 .
15.
Li H.
,
Boonnak N.
, and
Padwa A.
, Tetrahedron Lett. , 2011 , 52 , 2062 .
16.
Ondrus M.M.A.E.
, J. Org. Chem. , 2005 , 70 , 8638 .
17.
Zeng X.
,
Cheng G.
,
Shen J.
, and
Cui X.
, Org. Lett. , 2013 , 15 , 3022 .
18.
Verma A.K.
,
Joshi M.
, and
Singh V.P.
, Org. Lett. , 2011 , 13 , 1630 .
19.
Joshi M.
,
Tiwari R.
, and
Verma A.K.
, Org. Lett. , 2012 , 14 , 1106 .
20.
Joshi M.
,
Patel M.
,
Tiwari R.
, and
Verma A.K.
, J. Org. Chem. , 2012 , 77 , 5633 .
21.
Rattanangkool E.
,
Vilaivan T.
,
Sukwattanasinitt M.
, and
Wacharasindhu S.
, Eur. J. Org. Chem. , 2016 , 4347 .
22.
Fridkin G.
,
Boutard N.D.
, and
Lubell W.
, J. Org. Chem. , 2009 , 74 , 5603 .
23.
Hashmi A.S.K.
, and
Toste F.D.
(eds), Modern gold catalyzed synthesis. Wiley-VCH , Weinheim , 2012 .
24.
Corma A.
,
Leyva-Perez A.
, and
Sabater M.J.
, Chem. Rev. , 2011 , 111 , 1657 .
25.
Dorel R.
, and
Echavarren A.M.
, Chem. Rev. , 2015 , 115 , 9028 .
26.
Huple D.B.
,
Ghorpade S.
, and
Liu R.-S.
, Adv. Synth. Catal. , 2016 , 358 , 1348 .
27.
Pflästerer D.
, and
Hashmi A.S.K.
, Chem. Soc. Rev. , 2016 , 45 , 1331 .
28.
Davies P.W.
, and
Martin N.
, Org Lett. , 2009 , 11 , 2293 .
29.
Ueda H.
,
Yamaguchi M.
,
Kameya H.
,
Sugimoto K.
, and
Tokuyama H.
, Org Lett. , 2014 , 16 , 4948 .
30.
Li X.
,
Chen M.
,
Xie X.
,
Sun N.
,
Li S.
, and
Liu Y.
, Org Lett. , 2015 , 17 , 2984 .
31.
Zhang Y.
,
Donahue J.P.
, and
Li C.-J.
, Org. Lett. , 2007 , 9 , 627 .
32.
Matuda Y.
,
Naoe S.
,
Oishi S.
,
Fujii N.
, and
Ohno H.
, Chem. Eur. J. , 2015 , 21 , 1463 .
33.
Jin H.
,
Huang L.
,
Xie J.
,
Rudolph M.
,
Rominger F.
, and
Hashmi A.S.K.
, Angew. Chem., Int. Ed. , 2016 , 55 , 794 .
34.
He W.
,
Li C.
, and
Zhang L.
, J. Am. Chem. Soc. , 2011 , 133 , 8482 .
35.
Querard P.
,
Girard S.A.
,
Uhlig N.
, and
Li C.-J.
, Chem. Sci. , 2015 , 6 , 7332 .
36.
Chen M.
,
Sun N.
,
Chen H.
, and
Liu Y.
, Chem. Commun. , 2016 , 52 , 6324 .
37.
Phan N.T.S.
,
Sluys M.V.D.
, and
Jones C.W.
, Adv. Synth. Catal. , 2006 , 348 , 609 .
38.
Poliakoff M.
,
Fitzpatrick J.M.
,
Farren T.R.
, and
Anastas P.T.
, Science , 2002 , 297 , 807 .
39.
Polshettiwar V.
,
Luque R.
,
Fihri A.
,
Zhu H.
,
Bouhrara M.
, and
Basset J.-M.
, Chem. Rev. , 2011 , 111 , 3036 .
40.
Baig R.B.N.
, and
Varma R.S.
, Chem. Commun. , 2013 , 49 , 752 .
41.
Wang D.
, and
Astruc D.
, Chem. Rev. , 2014 , 114 , 6949 .
42.
Yang W.
,
Wei L.
,
Yi F.
, and
Cai M.
, Tetrahedron , 2016 , 72 , 4059 .
43.
Li P.
,
Wang L.
,
Zhang L.
, and
Wang G.-W.
, Adv. Synth. Catal. , 2012 , 354 , 1307 .
44.
Tsai F.-Y.
,
Lin B.-N.
,
Chen M.-J.
,
Mou C.-Y.
, and
Liu S.-T.
, Tetrahedron , 2007 , 63 , 4304 .
45.
Wang Z.-Q.
,
Zhang X.
,
Yu L.-T.
,
Mao W.-T.
,
Chen C.-Z.
, and
Xu K.
, Org. Biomol. Chem. , 2015 , 13 , 6931 .
