Abstract
A ligand-free palladium-catalysed oxidative Heck reaction of various arylboronic acids with 4-vinylpyridine has been developed, achieving (E)-4-styrylpyridines with high selectively in moderate to good yields. A plausible mechanism for the formation of (E)-4-styrylpyridines has been proposed.
References
1.
Iwase Y.
,
Kamada K.
,
Ohta K.
, and
Kondo K.
, J. Mater. Chem. , 2003 , 13 , 1575 .
2.
Kumar U.
,
Kato T.
, and
Frechet J.M.J.
, J. Am. Chem. Soc. , 1992 , 114 , 6630 .
3.
Chen G.
,
Shan W.
,
Wu Y.
,
Ren L.
,
Dong J.
, and
Ji Z.
, Chem. Pharm. Bull. , 2005 , 53 , 1587 .
4.
Das A.
,
Jeffery J.C.
,
Maher J.P.
,
McCleverty J.A.
,
Schatz E.
,
Ward M.D.
, and
Wollermann G.
, Inorg. Chem. , 1993 , 32 , 2145 .
5.
Lewis J.D.
, and
Moore J.N.
, J.C.S.Dalton Trans. , 2004 , 1376 .
6.
Hauser S.A.
,
Korinth V.
,
Herdtweck E.
,
Cokoja M.
,
Herrmann W.A.
, and
Kühn F.E.
, Eur. J. Inorg. Chem. , 2010 , 4083 .
7.
Suzuki T.
,
Suzuki Y.
,
Oda N.
,
Ohkubo J.
, and
Shinozaki H.
, J. Phys. Chem. B , 2007 , 111 , 8823 .
8.
Kaliappan R.
,
Kaanumalle L.S.
,
Natarajan A.
, and
Ramamurthy V.
, Photochem. Photobiol. Sci. , 2006 , 5 , 925 .
9.
To T.T.
,
Barnes C.E.
, and
Burkey T.J.
, Organometallics , 2004 , 23 , 2708 .
10.
Chen W.
,
Xi C.
, and
Yang K.
, Appl. Organometal. Chem. , 2007 ; 21 , 641 .
11.
Patel S.A.
,
Patel K.N.
,
Sinha S.
,
Kamath B.V.
, and
Bedekar A.V.
, J. Mol. Catal. A: Chem. , 2010 , 332 , 70 .
12.
Najman R.
,
Cho J.K.
,
Coffey A.F.
,
Davies J.W.
, and
Bradley M.
, Chem. Commun. , 2007 , 5031 .
13.
Bolliger J.L.
,
Blacque O.
, and
Frech C.M.
, Chem. Eur. J. , 2008 , 14 , 7969 .
14.
Chen W.
,
Xi C.
, and
Wu Y.
, J. Organometal. Chem. , 2007 , 692 , 4381 .
15.
Zhang Z.
, and
Wang Z.
, J. Org. Chem. , 2006 , 71 , 7485 .
16.
Bergbreiter D.E.
, and
Furyk S.
, Green Chem. , 2004 , 6 , 280 .
17.
Berthiol F.
,
Feuerstein M.
,
Doucet H.
, and
Santelli M.
, Tetrahedron Lett. , 2002 , 43 , 5625 .
18.
Miyaura N.
, and
Suzuki A.
, Chem. Rev. , 1995 , 95 , 2457 .
19.
Su Y.
, and
Jiao N.
, Curr. Org. Chem. , 2011 , 15 , 3362
20.
Karimi B.
,
Behzadnia H.
,
Elhamifar D.
,
Akhavan P.F.
,
Esfahani F.K.
, and
Zamani A.
, Synthesis , 2010 , 1399
21.
Qin C.M.
,
Wu H.Y.
,
Chen J.X.
,
Liu M.C.
,
Cheng J.
,
Su W.K.
, and
Ding J.C.
, Org. Lett. , 2008 , 10 , 1537 .
22.
Qin C.M.
,
Chen J.X.
,
Wu H.Y.
,
Cheng J.
,
Zhang Q.
,
Zuo B.
,
Su W.K.
, and
Ding J.C.
, Tetrahedron Lett. , 2008 , 49 , 1884 .
23.
Qin C.M.
,
Wu H.Y.
,
Cheng J.
,
Chen X.A.
,
Liu M.C.
,
Zhang W.W.
,
Su W.K.
, and
Ding J.C.
J. Org. Chem. , 2007 , 72 , 4102 .
24.
Zhang Q.
,
Chen J.X.
,
Liu M.C.
,
Wu H.Y.
,
Cheng J.
,
Qin C.M.
,
Su W.K.
, and
Ding J.C.
, Synlett , 2008 , 935 .
25.
Xu X.L.
,
Chen J.X.
,
Gao W.X.
,
Wu H.Y.
,
Ding J.C.
, and
Su W.K.
, Tetrahedron , 2010 , 66 , 2433 .
26.
Lu W.
,
Chen J.X.
,
Liu M.C.
,
Ding J.C.
,
Gao W.X.
, and
Wu H.Y.
, Org. Lett. , 2011 , 13 , 6114 .
27.
Enquist P.-A.
,
Nilsson P.
,
Sjöberg P.
, and
Larhed M.
, J. Org. Chem. , 2006 , 71 , 8779 .
28.
Lindh J.
,
Sävmarker J.
,
Nilsson P.
,
Sjçberg P.J.R.
, and
Larhed M.
, Chem. Eur. J. , 2009 , 15 , 4630 .
29.
Chandrasekhar V.
, and
Narayanan R.
, Tetrahedron Lett. , 2011 , 52 , 3527 .
30.
Kantchev E.A.B.
,
Peh G.-R.
,
Zhang C.
, and
Ying J. Y.
, Org. Lett. , 2008 , 10 , 3949 .
31.
Gibson H.W.
, and
Bailey F.C.
, Can. J. Chem. , 1975 , 53 , 2162 .
32.
Lucenti E.
,
Cariati E.
,
Dragonetti C.
,
Manassero L.
, and
Tessore F.
, Organometallics , 2004 , 23 , 687 .
33.
Horwitz L.
, J. Org. Chem. , 1956 , 21 , 1039 .
34.
Percino M.J.
,
Chapela V.M.
,
Montiel L.-F.
,
Perez-Gutierrez E.
, and
Maldonado J.L.
, Chem. Pap. , 2010 , 64 , 360 .
35.
Baker B.R.
, and
Gibson R.E.
, J. Med. Chem. , 1971 , 14 , 315 .
36.
Hewlin M.J.E.
, and
Salter R.
, Synthesis , 2007 , 2164 .