Abstract
A novel reaction between 1-(2,2-dibromovinyl)-2-(phenylethynyl)benzene and imidazole/benzimidazole catalysed by CuI and Pd(OAc)2 gave the corresponding highly sterically hindered diynes via a cascade elimination/Ullmann-type C–N coupling process.
Keywords
References
1.
Saluja S.
,
Zou R.
,
Drach J.C.
, and
Townsend L.B.
J. Med. Chem. , 1996 , 39 , 881 .
2.
Hauel N.H.
,
Nar H.
,
Priepke H.
,
Ries U.
,
Stassen J.-M.
, and
Wienen W.
, J. Med. Chem. , 2002 , 45 , 1757 .
3.
Morphy R.
, and
Rankovic Z.
, J. Med. Chem. , 2005 , 48 , 6524 .
4.
Gupta R.P.
,
Larroquette C.A.
, and
Agrawal K.C.
, J. Med. Chem. , 1982 , 25 , 1342 .
5.
Nadipuram A.K.
,
David W.M.
,
Kumar D.
, and
Kerwin S.M.
, Org. Lett. , 2002 , 4 , 4543 .
6.
Poloukhtine A.
, and
Popik V.V.
, J. Am. Chem. Soc. , 2007 , 129 , 12062 .
7.
Laroche C.
,
Li J.
, and
Kerwin S.M.
, J. Med. Chem. , 2011 , 54 , 5059 .
8.
Bergman R.G.
, Acc. Chem. Res. , 1973 , 6 , 25 .
9.
Shen B.
, and
Nonaka K.
, Curr. Med. Chem. , 2003 , 10 , 2317 .
10.
Galm U.
,
Hager M.H.
,
Lanen S.G.V.
,
Ju J.
,
Thorson J.S.
, and
Shen B.
, Chem. Rev. , 2005 , 105 , 739 .
11.
Liu Y.
, and
Wan J.-P.
, Chem. Asian. J. , 2012 , 7 , 1488 .
12.
Ma D.
, and
Cai Q.
, Acc. Chem. Res. , 2008 , 41 , 1450 .
13.
Monnier F.
, and
Taillefer M.
, Angew. Chem. Int. Ed. , 2009 , 48 , 6954 .
14.
Evano G.
,
Blanchard N.
, and
Toumi M.
, Chem. Rev. , 2008 , 108 , 3054 .
15.
Hassan J.
,
Sevignon M.
,
Gozzi C.
,
Schulz E.
, and
Lemaire M.
, Chem. Rev. , 2002 , 102 , 1359 .
16.
Fang Y.-Q.
, and
Lautens M.
, Org. Lett. , 2005 , 7 , 3549 .
17.
Fayol A.
,
Fang Y.-Q.
, and
Lautens M.
, Org. Lett. , 2006 , 8 , 4203 .
18.
Bryan C.S.
, and
Lautens M.
, Org. Lett. , 2008 , 10 , 4633 .
19.
Wang Z.-J.
,
Yang J.-G.
,
Yang F.
, and
Bao W.
, Org. Lett. , 2010 , 12 , 3034 .
20.
Nicolaus N.
,
Franke P.T.
, and
Lautens M.
, Org. Lett. , 2011 , 13 , 4236 .
21.
Chen W.
,
Zhang Y.
,
Zhang L.
,
Wang M.
, and
Wang L.
, Chem. Commun. , 2011 , 47 , 10476 .
22.
Zhou W.
,
Chen W.
, and
Wang L.
, Org. Biomol. Chem. , 2012 , 10 , 4172 .
23.
Nagamochi M.
,
Fang Y.-Q.
, and
Lautens M.
, Org. Lett. , 2007 , 9 , 2955 .
