Abstract
A series of chiral di-N-heterocyclic carbene (NHC) dipalladium complexes, [{PdPyCl2}2(di-NHC)], in which di-NHC represents a di-imidazolylidene, featuring an (S)-3,3′-dimethyl-2,2′-dimethoxy-1,1′-binaphthalene spacer between the carbene units, have been prepared. The influence of ligand size on the catalytic activity of these complexes in the Suzuki reaction of phenylboronic acid with p-bromotoluene has been investigated. The most sterically hindered complex, bearing the di-isopropylphenyl group, showed the greatest catalytic activity, and it is active for various aryl halides with different electronic and steric properties.
References
1.
Chartoire A.
and
Nolan S.
, RSC Catalysis Series , 2015 , 21 , 139 .
2.
Glorius S.W.F.
, Acc. Chem. Res. , 2008 , 41 , 1523 .
3.
Fortman G.C.
and
Nolan S.P.
, Chem. Soc. Rev. , 2011 , 40 , 5151 .
4.
Chauhan P.
and
Enders D.
, Angew. Chemie. , 2014 , 53 , 1485 .
5.
Baskakov D.
,
Herrmann W.A.
,
Herdtweck E.
and
Hoffmann S.D.
, Organometallics , 2007 , 26 , 626 .
6.
Li W.
and
Wiesenfeldt M.P.
, J. Am. Chem. Soc. , 2017 , 139 , 2585 .
7.
Gung B.W.
,
Holmes M.R.
,
Jones C.A.
,
Ma R.
and
Barnes C.L.
, Tetrahedron Lett. , 2016 , 57 , 3912 .
8.
Holmes M.R.
,
Manganaro J.F.
,
Barnes C.L.
and
Lukas B.
, Synthesis , 2015 , 47 , 924 .
9.
Kumar R.
,
Hoshimoto Y.
,
Yabuki H.
and
Ohashi M.
, J. Am. Chem. Soc. , 2015 , 137 , 11838 .
10.
Gilani M.A.
and
Rais E.
, Synlett. , 2015 , 26 , 1638 .
11.
Kundig E.P.
,
Jia Y.
,
Katayev D.
and
Nakanishi M.
, Pure. Appl. Chem. , 2012 , 84 , 1741 .
12.
Wang F.J.
,
Liu L.J.
,
Wang W.F.
,
Li S.K.
and
Shi M.
, Coord. Chem. Rev. , 2012 , 256 , 804 .
13.
Liu Z.
,
Zhang T.
and
Shi M.
, Organometallics , 2008 , 27 , 2668 .
14.
van Veldhuizen J.J.
,
Garber S.B.
,
Kingsbury J.S.
and
Hoveyda A.H.
, J. Am. Chem. Soc. , 2002 , 124 , 4954 .
15.
Larsen A.O.
,
Leu W.
,
Oberhuber C.N.
,
Campbell J.E.
and
Hoveyda A.H.
, J. Am. Chem. Soc. , 2004 , 126 , 11130 .
16.
Chianese A.R.
and
Crabtree R.H.
, Organometallics , 2005 , 24 , 4432 .
17.
Yang L.
,
Zhao J.
,
Li Y.
,
Ge K.
,
Zhuang Y.
,
Cao C.S.
and
Shi Y.H.
, Inorg. Chem. Commun. , 2012 , 22 , 33 .
18.
Du Y.
,
Liang B.
,
Yang F.
,
Shi Y.
,
Li X.
,
Pang G.
and
Cao C.
, Transition. Met. Chem. , 2017 , 42 , 193 .
19.
Ge K.
,
Cao C.
,
Liu G.
,
Li Y.
,
Zhang J.
,
Pang G.
and
Shi Y.
, Z. Anorg. Allg. Chem. , 2014 , 640 , 444 .
20.
Wang G.
,
Liu G.
,
Du Y.
,
Li W.
,
Yin S.
,
Wang S.
,
Shi Y.
and
Cao C.
, Transition. Met. Chem. , 2014 , 39 , 691 .
21.
Zhao J.
,
Yang L.
,
Ge K.
,
Chen Q.
,
Zhuang Y.
,
Cao C.
and
Shi Y.
, Inorg. Chem. Commun. , 2012 , 20 , 326 .
22.
Stock H.T.
and
Kellogg R.M.
, J. Org. Chem. , 1996 , 61 , 3093 .
23.
Wu H.
,
Jin C.
,
Huang G.L.
,
Wang L.J.
,
Jiang J.L.
and
Wand L.Y.
, Sci. Chi. Chem. , 2011 , 54 , 951 .
