Abstract
Pd(PPh3)4 in PEG-400 is shown to be a highly efficient catalyst for the Stille cross-coupling reactions of various organotin compounds with aryl bromides. The reaction could be conducted at 80 °C using NaOAc as base, yielding a variety of biaryls, alkynes and alkenes in good to excellent yields. The isolation of the products was readily performed by extraction with petroleum ether and the Pd(PPh3)4/PEG-400 system could be easily recycled and reused five times without any significant loss of activity.
References
1.
Stille J.K.
, Angew. Chem., Int. Ed. Engl. , 1986 , 25 , 508 .
2.
Mitchell T.N.
, Synthesis , 1992 , 803 .
3.
Tang H.
,
Menzel K.
, and
Fu G. C.
, Angew. Chem., Int. Ed. , 2003 , 42 , 5079 .
4.
Espinet P.
, and
Echavarren A. M.
, Angew. Chem., Int. Ed. , 2004 , 43 , 4704 .
5.
Cordovilla C.
,
Bartolome C.
,
Martinez-Ilarduya J. M.
, and
Espinet P.
, ACS Catal. , 2015 , 5 , 3040 .
6.
Thibonnet J.
,
Abarbri M.
,
Parrain J.-C.
, and
Duchene A.
, J. Org. Chem. , 2002 , 67 , 3941 .
7.
Echavarren A.M.
, Angew. Chem., Int. Ed. , 2005 , 44 , 3962 .
8.
Vaz B.
,
Alvarez R.
,
Bruckner R.
, and
de Lera A. R.
, Org. Lett. , 2005 , 7 , 545 .
9.
Cherry K.
,
Parrain J.-C.
,
Thibonnet J.
,
Duchene A.
, and
Abarbri M.
, J. Org. Chem. , 2005 , 70 , 6669 .
10.
Pchalek K.
, and
Hay M. P.
, J. Org. Chem. , 2006 , 71 , 6530 .
11.
Revell J.D.
, and
Ganesan A.
, Org. Lett. , 2002 , 4 , 3071 .
12.
Miao W.
, and
Chan T. H.
, Org. Lett. , 2003 , 5 , 5003 .
13.
Mathews C.J.
,
Smith P. J.
, and
Welton T.
, Chem. Commun. , 2000 , 1249 .
14.
Cai M.
,
Wang Y.
, and
Hao W.
, Green Chem. , 2007 , 9 , 1180 .
15.
Khedkar M.V.
,
Sasaki T.
, and
Bhanage B. M.
, ACS Catal. , 2013 , 3 , 287 .
16.
Chandrasekhar S.
,
Narsihmulu C.
,
Sultana S. S.
, and
Reddy N. R.
, Org. Lett. , 2002 , 4 , 4399 .
17.
Declerck V.
,
Colacino E.
,
Bantreil X.
,
Martinez J.
, and
Lamaty F.
, Chem. Commun. , 2012 , 48 , 11778 .
18.
Li J.-H.
,
Liu W.-J.
, and
Xie Y.-X.
, J. Org. Chem. , 2005 , 70 , 5409 .
19.
Liu L.
,
Zhang Y.
, and
Wang Y.
, J. Org. Chem. , 2005 , 70 , 6122 .
20.
Wang L.
,
Zhang Y.
,
Liu L.
, and
Wang Y.
, J. Org. Chem. , 2006 , 71 , 1284 .
21.
Ackermann L.
, and
Vicente R.
, Org. Lett. , 2009 , 11 , 4922 .
22.
Zhou Q.
,
Wei S.
, and
Han W.
, J. Org. Chem. , 2014 , 79 , 1454 .
23.
Zhao H.
,
Cheng M.
,
Zhang J.
, and
Cai M.
, Green. Chem. , 2014 , 16 , 2515 .
24.
Candeias N.R.
,
Branco L. C.
,
Gois P. M. P.
,
Afonso C. A. M.
, and
Trindade A. F.
, Chem. Rev. , 2009 , 109 , 2703 .
25.
Andrade C.K. Z.
, and
Alves L. M.
, Curr. Org. Chem. , 2005 , 9 , 195 .
26.
Chen J.
,
Spear S. K.
,
Huddleston J. G.
, and
Rogers R. D.
, Green Chem. , 2005 , 7 , 64 .
27.
Zhou W.-J.
,
Wang K.-H.
, and
Wang J.-X.
, Adv. Synth. Catal. , 2009 , 351 , 1378 .
28.
Zhou W.-J.
,
Wang K.-H.
, and
Wang J.-X.
, J. Org. Chem. , 2009 , 74 , 5599 .
29.
Logue M.W.
, and
Teng K.
, J. Org. Chem. , 1982 , 47 , 2549 .
30.
Lipshutz B.H.
,
Keil R.
, and
Barton J. C.
, Tetrahedron Lett. , 1992 , 33 , 5861 .
31.
Zhang H.X.
,
Guibe F.
, and
Balavoine G.
, J. Org. Chem. , 1990 , 55 , 1857 .
32.
Rosa G.R.
,
Rosa C. H.
,
Rominger F.
,
Dupont J.
, and
Monteiro A. L.
, Inorg. Chim. Acta , 2006 , 359 , 1947 .
33.
Liang B.
,
Dai M.
,
Chen J.
, and
Yang Z.
, J. Org. Chem. , 2005 , 70 , 391 .
34.
Cai M.
,
Zhou Z.
, and
Jiang J.
, Eur. J. Org. Chem. , 2006 , 1400 .
35.
Molander G.A.
, and
Brown A. R.
, J. Org. Chem. , 2006 , 71 , 9681 .
36.
Cai M.-Z.
,
Song C.-S.
, and
Huang X.
, Synthesis , 1997 , 521 .