Abstract
An effective and promising Ni/Cu catalytic system for the coupling of aryl iodides with various terminal alkynes has been developed. For the first time the readily available chiral amino alcohol has been employed as the ligand for the Pd-free Sonogashira coupling reaction.
References
1.
Tamao K.
, Comprehensive organic synthesis , Vol. 3 , eds
Trost B.M.
, and
Fleming I.
, Pergamon Press , New York , 1991 , pp. 435 –480 .
2.
Knight D.W.
, in Comprehensive organic synthesis , Vol. 3 , eds
Trost B.M.
, and
Fleming I.
, Pergamon Press , New York , 1991 , pp. 481 –520 .
3.
Sonogashira K.
, Comprehensive organic synthesis , Vol. 3 , eds
Trost B.M.
, and
Fleming I.
, Pergamon Press , New York , 1991 , pp. 521 –549 .
4.
Chinchilla R.
, and
Najera C.
, Chem. Rev. , 2007 , 107 , 874 .
5.
Liu D.
,
Xie Z.
,
Ma L.
, and
Lin W.
, Inorg. Chem. , 2010 , 49 , 9107 .
6.
Belema M.
, and
Kadow J.F.
, PCT, WO 2010117977, 2010 .
7.
Doucet H.
, and
Hierso J.-C.
, Angew. Chem. Int. Ed. , 2007 , 46 , 834 .
8.
Fukuyama T.
,
Shinmen M.
, and
Nishitani S.
, Org. Lett. , 2002 , 4 , 1691 .
9.
Li J.-H.
,
Wang D.-P.
, and
Xie Y.-X.
, J. Org. Chem. , 2006 , 71 , 379 .
10.
Anastasia L.
, and
Negishi E.
, Org. Lett. , 2001 , 3 , 3111 .
11.
Li J.-H.
,
Zhu Q.-M.
, and
Xie Y.-X.
, J. Org. Chem. , 2005 , 70 , 4393 .
12.
Li J.-H.
,
Wang D.-P.
, and
Xie Y.-X.
, Eur. J. Org. Chem. , 2005 , 4256 .
13.
Son S.U.
,
Jang Y.
,
Park J.
,
Na H.B.
,
Park H.M.
,
Yun H.J.
,
Lee J.
, and
Hyeon T.
, J. Am. Chem. Soc. , 2004 , 126 , 5026 .
14.
Corma A.
,
González-Arellano C.
,
Iglesias M.
, and
Sánchez F.
, Angew. Chem., Int. Ed. , 2007 , 46 , 7820 .
15.
Park S.
,
Kim M.
,
Koo D.H.
, and
Chang S.
, Adv. Synth. Catal. , 2004 , 346 , 1638 .
16.
Gujadhur R.K.
,
Bates C.G.
, and
Venkataraman D.
, Org. Lett. , 2001 , 3 , 4315 .
17.
Ma D.
, and
Liu F.
, Chem. Commun. , 2004 , 1934 .
18.
Zuidema E.
, and
Bolm C.
, Chem. Eur. J. , 2010 , 16 , 4181 .
19.
Carril M.
,
Correa A.
, and
Bolm C.
, Angew. Chem. Int. Ed. , 2008 , 47 , 4862 .
20.
Mao J.
,
Xie G.
,
Wu M.
,
Guo J.
, and
Ji S.
, Adv. Synth. Catal. , 2008 , 350 , 2477 .
21.
Wang L.
,
Li P.
, and
Zhang Y.
, Chem. Commun. , 2004 , 514 .
22.
Huang H.
,
Jiang H.
,
Chen K.
, and
Liu H.
, J. Org. Chem. , 2008 , 73 , 9061 .
23.
Finke A.D.
,
Elleby E.C.
,
Boyd M.J.
,
Weissman H.
, and
Moore J.S.
, J. Org. Chem. , 2009 , 74 , 8897 .
24.
Panda B.
, and
Sarkar T.K.
, Chem. Commun. , 2010 , 46 , 3131 .
25.
Mao J.
,
Guo J.
,
Song H.
, and
Ji S.
, Tetrahedron , 2008 , 64 , 1383 .