Abstract
1,4,7-Trimethyl-1,4,7-triazacyclononane (tmtacn, a cyclic trident-ligand) has been developed as a facile and efficient catalyst for Cu-catalysed homocoupling of terminal alkynes at room temperature. A variety of 1,3-diynes have been synthesised in excellent yields with a catalyst loading on a scale of 0.1–0.5 mol% CuBr–tmtacn.
References
1.
Liu J.
,
Lam J.W.Y.
, and
Tang B.Z.
, Chem. Rev. , 2009 , 109 , 5799 .
2.
Wang L.G.
,
Yu X.Q.
,
Feng X.J.
, and
Bao M.
, J. Org. Chem. , 2013 , 78 , 1693 .
3.
Pérez J.M.
,
Cano R.
,
Yus M.
, and
Ramón D.J.
, Synthesis , 2013 , 10 , 1373 .
4.
Li C.H.
,
Yuan G.Q.
,
Qi C.R.
, and
Jiang H.F.
, Tetrahedron , 2013 , 69 , 3135 .
5.
Susanto W.
,
Chu C.Y.
,
Ang W.J.
,
Chou T.C.
,
Lo L.C.
, and
Lam Y.
, J. Org. Chem. , 2012 , 77 , 2729 .
6.
Chen S.N.
,
Wu W.Y.
, and
Tsai F.Y.
, Green Chem. , 2009 , 11 , 269 .
7.
Li J.
,
Liang Y.
, and
Zhang X.
, Tetrahedron , 2005 , 61 , 1903 .
8.
Zhu M.
,
Ning M.
,
Fu W.J.
,
Xu C.
, and
Zou G.L.
, Bull. Korean Chem. Soc. , 2012 , 33 , 1325 .
9.
Hay A.S.
, J. Org. Chem. , 1962 , 27 , 3320 .
10.
Adimurthy S.
,
Malakar S.
, and
Beifuss U.
, J. Org. Chem. , 2009 , 74 , 5649 .
11.
Zhang S.L.
,
Liu X.Y.
, and
Wang T.Q.
, Green Chem. , 2011 , 13 , 843 .
12.
Li L.
,
Wang L.
,
Zhang G.
, and
Liu Q.
, Tetrahedron Lett. , 2009 , 50 , 4033 .
13.
Kusuda A.
,
Xu X.H.
,
Wang X.
,
Tokunaga E.
, and
Shibata N.
, Green Chem. , 2011 , 13 , 843 .
14.
Li S.T.
,
Schnabel T.
,
Lysenko S.
,
Brandhorst K.
, and
Tamm M.
, Chem. Commun. , 2013 , 49 , 7189 .
15.
Ma Z.Y.
,
Wang X.Y.
,
Wei S.Y.
,
Yang H.L.
,
Zhang F.W.
,
Wang P.
,
Xie M.
, and
Ma J.T.
, Catal. Commun. , 2013 , 39 , 24 .
16.
Liu Y.Y.
,
Wang C.P.
,
Wang X.B.
, and
Wan J.P.
, Tetrahedron Lett. , 2013 , 30 , 3953 .
17.
Toummini D.
,
Ouazzani F.
, and
Taillefer F.
, Org. Lett. , 2013 , 18 , 4690 .
18.
Vilhelmsen M.H.
,
Jensen J.
,
Tortzen C.J.
, and
Nielsen M.B.
, Eur. J. Org. Chem. , 2013 , 701 .
19.
Oishi T.
,
Yamaguchi K.
, and
Misuno N.
, ACS Catal. , 2011 , 1 , 1351 .
20.
Cheng T.P.
,
Liao B.S.
,
Liu Y.H.
,
Peng S.H.
, and
Liu S.T.
, Dalton Trans. , 2012 , 41 , 3468 .
21.
Schmidt R.
,
Thorwirth R.
,
Szuppa T.
,
Stolle A.
,
Ondruschka B.
, and
Hopf H.
, Chem. Eur. J. , 2011 , 17 , 8129 .
22.
Berkessel A.
, and
Sklorz C.A.
, Tetrahedron Lett. , 1999 , 40 , 7965 .
23.
Surry D.S.
, and
Buchwald S.L.
, Chem. Sci. , 2010 , 1 , 13 .
24.
Wang L.
,
Yan J.C.
,
Li P.H.
,
Wang M.
, and
Su C.N.
, J. Chem. Res. , 2005 , 112 .
25.
He Y.
, and
Cai C.
, Catal. Sci. Technol. , 2012 , 2 , 1126 .
26.
Yin K.
,
Li C.J.
,
Li J.
, and
Jia X.S.
, Green Chem. , 2011 , 13 , 591 .
27.
Merkul E.
,
Urselmann D.
, and
Mueller T.J.
, Eur. J. Org. Chem. , 2011 , 238 .
28.
Chen L.R.
,
Lemma B.E.
,
Richa J.S.
, and
Mack J.
, Green Chem. , 2014 , 16 , 1101 .
29.
Yao P.
, J. Chem. Res. , 2013 , 37 , 174 .
