Abstract
The palladium acetate-catalysed dehalogenation of biaryl halides has been investigated in room temperature ionic liquids with pyridine acting as a co-solvent. The significant effect of pyridine in conjunction with Pd(OAc)2 in [bmim][PF6] gave excellent results in the dehalogenation of biaryl iodines and bromides. The pyridine activated the C2-H of the imidazolium salt to be the source of hydrogen. The separation of desired product was easily performed by extraction with diethyl ether and the Pd(OAc)2–[bmim][PF6] system could be recycled five times with only a small decrease in activity. This procedure represents an environmentally friendly method for the preparation of biaryl compounds without the use of complex ligands.
References
1.
Miyaura N.
, and
Suzuki A.
, Chem. Rev. , 1995 , 95 , 2457 .
2.
Baudoin O.
,
Cesario M.
,
Guenard D.
, and
Gueritte F.
, J. Org. Chem. , 2002 , 67 , 1199 .
3.
Wong K.
,
Hung T.
,
Lin Y.
,
Wu C.
,
Lee G.H.
,
Peng S.M.
,
Chou C.
, and
Su Y.
, Org. Lett. , 2002 , 4 , 513 .
4.
Kotha S.
,
Lahiri K.
, and
Kashinath D.
, Tetrahedron , 2002 , 58 , 9633 .
5.
Nicolaou K.C.
,
Boddy C.N.C.
,
Brase S.
, and
Winssinger N.
, Angew. Chem. Int. Ed. , 1999 , 38 , 2096 .
6.
Parry R.J.
,
Li Y.
, and
Gomez E.E.
, J. Am. Chem. Soc. , 1992 , 114 , 5946 .
7.
Dorman G.
,
Otszenski J.D.
, and
Prestwich G.D.
, J. Org. Chem. , 1995 , 60 , 2292 .
8.
Terstiege I.
, and
Maleczka R.E.
, J. Org. Chem. , 1999 , 64 , 342 .
9.
Wiener H.
,
Blum J.
, and
Sasson Y.
, J. Org. Chem. , 1991 , 56 , 6145 .
10.
Marques C.A.
,
Selva M.
, and
Tundo P.
, J. Org. Chem. , 1993 , 58 , 5256 .
11.
Zagorski M.G.
, and
Salomon R.G.
, J. Am. Chem. Soc. , 1984 , 106 , 1750 .
12.
Mitoma Y.
,
Nagashima S.
,
Simion C.
,
Simion A.
, and
Tashiro M.
, Environ. Sci. Technol. , 2001 , 35 , 4145 .
13.
Yoon N.M.
, and
Brown H.C.
, J. Am. Chem. Soc. , 1968 , 90 , 2927 .
14.
Stiles M.
, J. Org. Chem. 1994 , 59 , 5381 .
15.
Hutchins R.O.
,
Learn K.
,
El-Telbany F.
, and
Stercho Y.P.
, J. Org. Chem. , 1984 , 49 , 2438 .
16.
Brieger G.
, and
Nestrick T.
, J. Chem. Rev. , 1974 , 74 , 567 –580 .
17.
Viciu M.S.
,
Grasa G.A.
,
Nolan S.P.
, Organometallics , 2001 , 20 , 3607 .
18.
Welton T.
, Chem. Rev. , 1999 , 99 , 2071 .
19.
Dupont J.
, Acc. Chem. Res. , 2011 , 44 , 1223 .
20.
Angell C.A.
,
Byrne N.
, and
Belieres J.
, Acc. Chem. Res. , 2007 , 40 , 1228 .
21.
Park S.B.
, and
Alper H.
, Org. Lett. , 2003 , 5 , 3209 .
22.
Vallin K.S.A.
,
Emilsson P.
,
Larhed M.
, and
Hallberg A.
, J. Org. Chem. , 2002 , 67 , 6243 .
23.
Xiao J.
, and
Shreeve J.M.
, J. Org. Chem. , 2005 , 70 , 3072 .
24.
Mathews C.J.
,
Smith P.J.
, and
Welton T.
, J. Molec. Catal. A: Chem. , 2004 , 214 , 27 .
25.
Corma A.
,
Garcý H.
, and
Leyva A.
, Tetrahedron , 2004 , 60 , 8553 .
26.
handy S.T.
, and
Zhang X.
, Org. Lett. , 2001 , 3 , 233 .
27.
Sirieix J.
,
Ossberger M.
,
Betzemeier B.
, and
Knochel P.
, Synlett , 2000 , 11 , 1613 .
28.
Mathews C.J.
,
Smith P.J.
,
Welton T.
,
White A.J.P.
, and
Williams D.J.
, Organometallics , 2001 , 20 , 3848 .
29.
Navarro O.
,
Kaur H.
,
Mahjoor P.
, and
Nolan S.P.
, J. Org. Chem. 2003 , 69 , 3173 .
30.
Tao B.
, and
Boykin D.W.
, J. Org. Chem. 2004 , 69 , 4330 .
31.
Leadbeater N.E.
, and
Marco M.
, Org. Lett. 2002 , 4 , 2973 .
32.
Yamada Y.M.A.
,
Takeda K.
,
Takahashi H.
, and
Ikegami S.
, Org. Lett. 2002 , 4 , 3371 .
33.
-Mañas M.M.
, and
Pleixats R.
, Acc. Chem. Res. , 2003 , 36 , 638 .
34.
Deshmukh R.R.
,
Rajagopal R.
, and
Srinivasan K.V.
, Chem. Commun. , 2001 , 1544 .
35.
Chen W.
, and
Xiao J.
, Organometallics , 2000 , 19 , 1123 .
36.
Herrmann W.A.
,
Köcher C.
,
Gooβen L.J.
, and
Artus G.R.J.
, Chem. Eur J. , 1996 , 2 , 772 .
37.
Köcher C.
, and
Herrmann W.A.
, J. Organomet. Chem. , 1997 , 532 , 261 .
38.
Clement N.D.
,
Cavell K.J.
,
Jones C.
, and
Elsevier C.J.
, Angew. Chem. Int. Ed. , 2004 , 43 , 1277 .
39.
Cavell K.J.
, and
McGuinness D.S.
, Coord. Chem. Rev. , 2004 , 248 , 671 .