N-Heterocyclic Carbene-Acetylamide Palladium Complexes and Their Catalytic Activities in Heck-Mizoroki Reactions

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
• 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 

10

The X-ray crystal data for compound 6 have been deposited in the CCDC with number 281153. Empirical formula: C₂₈H₁₉N₃; 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) Å^³; Space group: P2₁/c; Z = 4; D _calc  = 1.294 g/cm^³; F₀₀₀ = 832; Diffractometer: Rigaku AFC7R; Residuals: R1, wR2: 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: C₆₀H₄₈I₂N₆O₂Pd₂; 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) Å^³; Space group: P2₁/c; Z = 4; D _calc  = 1.321 g/cm^³; F₀₀₀ = 2720; Diffractometer: Rigaku AFC7R; Residuals: R1, wR2: 0.1167, 0.2771.