Abstract
A novel N-heterocyclic carbene-acetylamide ligand derived from
binaphthyl-2,2′-diamine (BINAM) and its dinuclear NHC-Pd(II)
complex as well as its corresponding complex bearing weakly coordinating
acetate counterions, have been successfully synthesized in good
yields. The dinuclear NHC-Pd(II) complex has been characterized
by X-ray diffraction. Moreover, we found that these complexes are
quite effective in Heck-Mizoroki reactions and give the
corresponding products in good to excellent yields.
Key words
N-heterocyclic carbene-acetylamide - dinuclear NHC-Pd(II)
complex - binaphthyl-2,2′-diamine - Heck-Mizoroki
reaction
References
1a
Gstottmayr CWK.
Bohm VPW.
Herdtweck E.
Grosche M.
Herrmann WA.
Angew.
Chem. Int. Ed.
2002,
41:
1363
1b
Arensten K.
Caddick S.
Cloke FGN.
Herring AP.
Hitchcock PB.
Tetrahedron Lett.
2004,
45:
3511
1c
Mata JA.
Chianese AR.
Miecznikowski JR.
Poyatos M.
Peris M.
Faller JW.
Crabtree RH.
Organometallics
2004,
23:
1253
1d
Crabtree RH.
J. Organomet. Chem.
2005,
690:
5451
1e
Dorta R.
Stevens ED.
Scott NM.
Chiara C.
Cavallo L.
Hoff CD.
Nolan SP.
J. Am. Chem. Soc.
2005,
127:
2485
2a
Herrmann WA.
Angew. Chem. Int.
Ed.
2002,
41:
1290
2b
Bourissou D.
Guerret O.
GabbaÏ FP.
Bertrand G.
Chem. Rev.
2000,
100:
39
2c
Herrmann WA.
Böhm VPW.
Gstöttmayr CWK.
Grosche M.
Reisinger C.
Weskamp T.
J. Organomet. Chem.
2001,
617-618:
616
2d
Enders D.
Gielen H.
J. Organomet. Chem.
2001,
617-618:
70
2e
Tulloch AAD.
Danopoulos AA.
Winston S.
Kleinhenz S.
Eastham G.
J. Chem. Soc., Dalton Trans.
2000,
4499
2f
Douthwaite RE.
Houghton J.
Kariuki BM.
Chem. Commun.
2004,
698
2g
Lee HM.
Zeng JY.
Hu CH.
Lee MT.
Inorg. Chem.
2004,
43:
6822
3a
Herrmann WA.
Elison M.
Fisher J.
Koecher C.
Artus GRJ.
Angew. Chem.
Int. Ed.
1995,
34:
2371
3b
Albert K.
Gisdakis P.
Rosch N.
Organometallics
1998,
17:
1608
3c
Zhang C.
Trudell ML.
Tetrahedron Lett.
2000,
41:
595
3d
Perry MC.
Cui X.-H.
Burgess K.
Tetrahedron: Asymmetry
2002,
13:
1969
3e
Lee H.-M.
Lu C.-Y.
Chen C.-Y.
Chen W.-L.
Lin H.-C.
Chiu
P.-L.
Cheng P.-Y.
Tetrahedron
2004,
60:
5807
3f
Marshall C.
Ward M.-F.
Harrison WTA.
Tetrahedron Lett.
2004,
45:
5703
3g
Clyne DS.
Jin J.
Genest E.
Gallucci JC.
RajanBabu TV.
Org. Lett.
2000,
2:
1125
3h
Kantchev EAB.
O’Brien CJ.
Organ MG.
Angew. Chem. Int. Ed.
2007,
46:
2768
4a
Huang J.
Grasa G.
Nolan SP.
Org. Lett.
1999,
1:
1307
4b
Stauffer SR.
Lee S.
Stambuli JP.
Hauck SI.
Hartwig JF.
Org. Lett.
2000,
2:
1423
4c
Lee S.
Hartwig JF.
J. Org. Chem.
2001,
66:
3402
4d
Yang C.
Lee HM.
Nolan SP.
Org.
Lett.
2001,
3:
1511
4e
Batey RA.
Shen M.
Lough AJ.
Org. Lett.
2002,
4:
1411
4f
Huang J.
Nolan SP.
J. Am. Chem. Soc.
1999,
121:
9889
4g
Lee HM.
Nolan SP.
Org. Lett.
2000,
2:
2053
4h
Zhang C.
Huang J.
Trudell ML.
Nolan SP.
J. Org. Chem.
1999,
64:
3804
4i
Zhang C.
Trudell ML.
Tetrahedron Lett.
2000,
41:
595
4j
Grasa GA.
Nolan SP.
Org.
Lett.
2001,
3:
119
5a
Huynh HV.
Le Van D.
Hahn FE.
Hor TSA.
J. Organomet. Chem.
2004,
689:
1766
5b
Jensen DR.
Schultz MJ.
Mueller JA.
Sigman MS.
Angew.
Chem. Int. Ed.
2003,
42:
3810
5c
Mueller JA.
Goller CP.
Sigman MS.
J. Am. Chem. Soc.
2004,
126:
9724
5d
Viciu MS.
Stevens ED.
Petersen JL.
Nolan SP.
Organometallics
2004,
23:
3752
5e
Singh R.
Viciu MS.
Kramareva N.
Navarro O.
Nolan SP.
Org.
Lett.
2005,
7:
1829
5f
Voges MH.
Romming C.
Tilset M.
Organometallics
1999,
18:
529
5g
Herrmann WA.
Kocher C.
Angew. Chem.
Int. Ed.
1997,
36:
2163
6a
Zhang T.
Shi M.
Zhao M.-X.
Tetrahedron
2008,
64:
2412
6b
Zhang T.
Shi M.
Chem. Eur. J.
2008,
14:
3759
7a
Duan W.-L.
Shi M.
Rong G.-B.
Chem. Commun.
2003,
2916
7b
Xu Q.
Duan WL.
Lei ZY.
Zhu ZB.
Shi M.
Tetrahedron
2005,
61:
11225
7c
Chen T.
Jiang J.-J.
Xu Q.
Shi M.
Org. Lett.
2007,
9:
865 ; and references cited therein
8a
Shi M.
Qian H.-X.
Appl.
Organomet. Chem.
2005,
19:
1083
8b
Shi M.
Qian H.-X.
Tetrahedron
2005,
61:
4949
9
Zhang T.
Wang W.-F.
Gu X.-X.
Shi M.
Organometallics
2008,
27:
753 ; and references cited therein
10 The X-ray crystal data for compound 6 have been deposited in the CCDC with
number 281153. Empirical formula: C28 H19 N3 ;
Formula weight: 397.46; Crystal color, habit: colorless, prismatic;
Crystal dimensions: 0.480 × 0.378 × 0.216
mm; Crystal system: monoclinic; Lattice type: primitive; Lattice
parameters: a = 8.7871(8) Å, b = 25.373(3) Å, c = 9.3514(9) Å, β = 101.837(2)˚; V = 2040.6(3) ų ;
Space group: P 21 /c ; Z = 4;
D
calc
= 1.294 g/cm³ ;
F000 = 832; Diffractometer:
Rigaku AFC7R; Residuals: R 1, wR 2: 0.0548, 0.1023.
11 The X-ray crystal data of NHC-Pd(II)
complex 7 have been deposited in the CCDC
with number 601088. Empirical formula: C60 H48 I2 N6 O2 Pd2 ;
Formula weight: 1383.64; Crystal color, habit: colorless, prismatic;
Crystal dimensions: 0.138 × 0.115 × 0.040
mm; Crystal system: monoclinic; Lattice type: primitive; Lattice
parameters: a = 14.496(12) Å, b = 20.803(16) Å, c = 23.523(19) Å, β = 101.179(15)˚; V = 6959(10) ų ;
Space group: P 21 /c ; Z = 4;
D
calc
= 1.321
g/cm³ ; F000 = 2720;
Diffractometer: Rigaku AFC7R; Residuals: R 1, wR 2: 0.1167, 0.2771.
12a
Bondi A.
J. Phys. Chem.
1964,
68:
443
12b
Pyykko P.
Chem.
Rev.
1997,
97:
597
13
Masllorens J.
Moreno-Manas M.
Pla-Quintana A.
Roglans A.
Org. Lett.
2003,
5:
1559