Abstract
A reaction of acetals with dibenzylamine and alkynes to form propargylamines has been developed via the activation of both C(sp3)-O and C(sp)-H bonds by InCl3. The iminium ion has been found to be the key intermediate.
References
1.
Milroy L.G.
,
Zinzalla G.
,
Loiseau F.
,
Qian Z.
,
Prencipe G.
,
Pepper C.
,
Fegan C.
, and
Ley S.V.
, ChemMedChem , 2008 , 3 , 1922 .
2.
Dixon D.J.
,
Foster A.C.
,
Ley S.V.
, and
Reynolds D.J.
, J. Chem. Soc., Perkin Trans. 1 , 1999 , 1635 .
3.
Chowdhury A.D.
, and
Lahiri G.K.
, Chem. Commun. , 2012 , 48 , 3448 .
4.
Mukaiyama T.
, and
Murakami M.
, Synthesis , 1987 , 1043 .
5.
Maity P.
,
Srinivas H.D.
, and
Watson M.P.
, J. Am. Chem. Soc. , 2011 , 133 , 17142 .
6.
Bauer E.B.
, Synthesis , 2012 , 1131 .
7.
Nishibayashi Y.
, Synthesis , 2012 , 489 .
8.
Hattori G.
,
Matsuzawa H.
,
Miyake Y.
, and
Nishibayashi Y.
, Angew. Chem., Int. Ed. , 2008 , 47 , 3781 .
9.
Detz R.J.
,
Delville M.M.E.
,
Hiemstra H.
, and
van Maarseveen J.H.
, Angew. Chem., Int. Ed. , 2008 , 47 , 3777 .
10.
Hattori G.
,
Sakata K.
,
Matsuzawa H.
,
Tanabe Y.
,
Miyake Y.
, and
Nishibayashi Y.
, J. Am. Chem. Soc. , 2010 , 132 , 10592 .
11.
Yoo W.J.
,
Zhao L.
, and
Li C.J.
, Aldrichimica Acta , 2011 , 44 , 43 .
12.
Davis J.L.
,
Dhawan R.
, and
Arndtsen B.A.
, Angew. Chem., Int. Ed. , 2004 , 43 , 590 .
13.
Siamaki A.R.
,
Black D.A.
, and
Arndtsen B.A.
, J. Org. Chem. , 2008 , 73 , 1135 .
14.
Williams D.B.G.
,
Cullen A.
,
Fourie A.
,
Henning H.
,
Lawton M.
,
Mommsen W.
,
Nangu P.
,
Parkera J.
, and
Renison A.
, Green Chem. , 2010 , 12 , 1919 .
15.
Li W.
,
Li J.
,
Wu Y.
,
Fuller N.
, and
Markus M.A.
, J. Org. Chem. , 2010 , 75 , 1077 .
16.
Huang B.
,
Yao X.
, and
Li C.J.
, Adv. Synth. Catal. , 2006 , 348 , 1528 .
17.
Wei C.M.
,
Li Z.G.
, and
Li C.J.
, Org. Lett. , 2003 , 5 , 4473 .
18.
Chang L.L.
,
Yang J.
,
Wei Y.
, and
Ying J.Y.
, Adv. Synth. Catal. , 2009 , 351 , 2887 .
19.
Wei C.M.
, and
Li C.J.
, J. Am. Chem. Soc. , 2003 , 125 , 9584 .
20.
Zhang Y.
,
Li P.
,
Wang M.
, and
Wang L.
, J. Org. Chem. , 2009 , 74 , 4364 .
21.
Singh M.S.
, and
Raghuvanshi K.
, Tetrahedron , 2012 , 68 , 8683 .
22.
Samai S.
,
Nandi G.C.
, and
Singh M.S.
, Tetrahedron Lett. , 2010 , 51 , 5555 .
23.
Kobayashi S.
,
Arai K.
,
Yamakawa T.
,
Chen Y.J.
,
Salter M.M.
, and
Yamashita Y.
, Adv. Synth. Catal. , 2011 , 353 , 1927 .
24.
Sreedhar B.
,
Kumar A.S.
, and
Reddy P.S.
, Tetrahedron Lett. , 2010 , 51 , 1891 .
25.
Adimurthy S.
,
Malakar C.C.
, and
Beifuss U.
, J. Org. Chem. , 2009 , 74 , 5648 .
26.
Lee O.Y.
,
Law K.L.
,
Ho C.Y.
, and
Yang D.
, J. Org. Chem. , 2008 , 73 , 8829 .
27.
Zhang Y.J.
,
Dayoub W.
,
Chen G.R.
, and
Lemaire M.
, Green Chem. , 2011 , 13 , 2737 .
28.
Idzika K.R.
,
Cabaja J.
,
Soloducho J.
, and
Abdel-Fattahb A.A.A.
Helv. Chim. Acta , 2007 , 90 , 1672 –1680 .
29.
Xiang S.H.
,
Xu J.
,
Yuan H.Q.
, and
Huang P.Q.
, Synlett , 2010 , 1829 .