Catalytic Activities of a Bis(carbene)-Derived Nickel(II)-Pincer Complex in Kumada-Tamao-Corriu and Suzuki-Miyaura Coupling Reactions for the Synthesis of Biaryl Compounds

Abstract

The catalytic activities of a pincer type bis(imidazolin-2-ylidene)nickel(II) complex were evaluated. The complex was found to be an effective catalyst in the Kumada-Tamao-Corriu and Suzuki-Miyaura coupling reactions of a broad range of aryl-X (X = Br, Cl and F) compounds, providing a variety of biaryl compounds, generally in good yield.

nickel - N-heterocyclic carbenes - pincer ligands - Kumada-Tamao-Corriu coupling - Suzuki-Miyaura coupling

References

<A NAME="RF07107SS-1">1</A> For a recent review, see: Alberico D. Scott ME. Lautens M. Chem. Rev.  2007,  107:  174 

<A NAME="RF07107SS-2">2</A> Bringmann G. Menche D. Acc. Chem. Res.  2001,  34:  615 

<A NAME="RF07107SS-3">3</A> Hajduk PJ. Bures M. Praestgaard J. Fesik SW. J. Med. Chem.  2000,  43:  3443 

<A NAME="RF07107SS-4">4</A> Yamamoto T. Synlett  2003,  425 

<A NAME="RF07107SS-5">5</A> There are a number of books for Pd- and Ni-catalyzed cross-coupling reactions, see: de Meijere A. Diederich F. Metal-Catalyzed Cross-Coupling Reactions   2nd ed.:  Wiley-VCH; Weinheim: 2004. 

For recent reviews, see:

<A NAME="RF07107SS-6A">6a</A> Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 

<A NAME="RF07107SS-6B">6b</A> Bedford RB. Cazin CSJ. Holder D. Coord. Chem. Rev.  2004,  248:  2283 

<A NAME="RF07107SS-7">7</A> For a review, see: Kiplinger JL. Richmond TG. Osterberg CE. Chem. Rev.  1994,  94:  373 

For C-F bond activation by nickel (selected references), see:

<A NAME="RF07107SS-8A">8a</A> Kiso Y. Tamao K. Kumada M. J. Organomet. Chem.  1973,  50:  C12 

<A NAME="RF07107SS-8B">8b</A> Bohm VPW. Gstottmayr CWK. Weskamp T. Herrmann WA. Angew. Chem. Int. Ed.  2001,  40:  3387 

<A NAME="RF07107SS-8C">8c</A> Mongin F. Mojovic L. Guillamet B. Trecourt F. Queguiner G. J. Org. Chem.  2002,  67:  8991 

<A NAME="RF07107SS-8D">8d</A> Saeki T. Takashima Y. Tamao K. Synlett  2005,  1771 

<A NAME="RF07107SS-8E">8e</A> Yoshikai N. Mashima H. Nakamura E. J. Am. Chem. Soc.  2005,  127:  17978 

<A NAME="RF07107SS-8F">8f</A> Ackermann L. Born R. Spatz JH. Meyer D. Angew. Chem. Int. Ed.  2005,  44:  7216 

<A NAME="RF07107SS-8G">8g</A> Dankwardt JW. J. Organomet. Chem.  2005,  690:  932 

<A NAME="RF07107SS-8H">8h</A> Ackermann L. Born R. Spatz JH. Althammer A. Gschrei CJ. Pure Appl. Chem.  2006,  78:  209 

For C-F bond activation by palladium (selected references), see:

<A NAME="RF07107SS-9A">9a</A> Kim YM. Yu S. J. Am. Chem. Soc.  2003,  125:  1696 

<A NAME="RF07107SS-9B">9b</A> Widdowson DA. Wilhelm R. Chem. Commun.  2003,  578 

<A NAME="RF07107SS-10">10</A> Dankwardt JW. Angew. Chem. Int. Ed.  2004,  43:  2428 

<A NAME="RF07107SS-11">11</A> Sengupta S. Leite M. Raslan DS. Quesnelle C. Snieckus V. J. Org. Chem.  1992,  57:  4066 

For recent reviews, see:

<A NAME="RF07107SS-12A">12a</A> Crudden CM. Allen DP. Coord. Chem. Rev.  2004,  248:  2247 

<A NAME="RF07107SS-12B">12b</A> Kantchev EAB. O’Brien CJ. Organ MG. Angew. Chem. Int. Ed.  2007,  46:  2768 

<A NAME="RF07107SS-12C">12c</A> Kuhl O. Chem. Soc. Rev.  2007,  36:  592 

Compared to the Pd/NHC system, there are only a few reports on Ni/NHC system catalyzed coupling reactions, for example:

<A NAME="RF07107SS-13A">13a</A> For Grignard coupling, see: Matsubara K. Ueno K. Shibata Y. Organometallics  2006,  25:  3422 

<A NAME="RF07107SS-13B">13b</A> For Suzuki-Miyaura coupling, see: Lee C.-C. Ke W.-C. Chan K.-T. Lai C.-L. Hu C.-H. Lee H.-M. Chem. Eur. J.  2007,  13:  582 

<A NAME="RF07107SS-13C">13c</A> For amination, see: Desmarets C. Schneider R. Fort Y. J. Org. Chem.  2002,  67:  3029 

<A NAME="RF07107SS-14A">14a</A> Blakey SB. MacMillan DWC. J. Am. Chem. Soc.  2003,  125:  6046 

<A NAME="RF07107SS-14B">14b</A> Powell DA. Maki T. Fu GC. J. Am. Chem. Soc.  2005,  127:  510 

<A NAME="RF07107SS-15">15</A> Inamoto K. Kuroda J.-I. Hiroya K. Noda Y. Watanabe M. Sakamoto T. Organometallics  2006,  25:  3095 

For reviews on NHC-derived metal-pincer complexes, see:

<A NAME="RF07107SS-16A">16a</A> Peris E. Crabtree RH. Coord. Chem. Rev.  2004,  248:  2239 

<A NAME="RF07107SS-16B">16b</A> Pugh D. Danopoulos A. Coord. Chem. Rev.  2007,  251:  610 

Compared to Pd-pincer complexes, reports on the synthesis and catalytic activities of Ni-pincer complexes are much rarer, for example:

<A NAME="RF07107SS-17A">17a</A> For NCN-type, see: Gossage RA. van de Kuil LA. van Koten G. Acc. Chem. Res.  1998,  31:  423 ; and references therein

<A NAME="RF07107SS-17B">17b</A> For NNN-type, see: Baldovino-Pantaleon O. Hernandez-Ortega S. Morales-Morales D. Inorg. Chem. Commun.  2005,  8:  955 

<A NAME="RF07107SS-17C">17c</A> For PNP-type, see: Liang L.-C. Chien P.-S. Lin J.-M. Huang M.-H. Huang Y.-L. Liao J.-H. Organometallics  2006,  25:  1399 

<A NAME="RF07107SS-18">18</A>

Preliminary results on nickelacycle 1 catalyzed Suzuki-Miyaura coupling has been reported previously, see reference 15.

<A NAME="RF07107SS-19">19</A>

For preparation of nickelacycle 1, see reference 15.

<A NAME="RF07107SS-20A">20a</A>

Compared to Herrmann’s Ni-NHC monodentate system, [8b] the rate of this reaction with nickelacycle 1 is considerably slower.

<A NAME="RF07107SS-20B">20b</A>

Herrmann proposed a polar reaction mechanism with his system in the Grignard couplings of aryl fluorides. [8b]

<A NAME="RF07107SS-20C">20c</A> Involvement of a SET (single electron transfer) mechanism in the Grignard couplings of aryl chlorides in the presence of amido pincer complexes of nickel was suggested recently, see: Wang Z.-X. Wang L. Chem. Commun.  2007,  2423 

<A NAME="RF07107SS-21">21</A> Percec V. Golding GM. Smidrkal J. Weichold O. J. Org. Chem.  2004,  69:  3447 

<A NAME="RF07107SS-22">22</A> Suresh CRM. Krishna RGS. Synthesis  1987,  23 

<A NAME="RF07107SS-23">23</A> Denmark SE. Ober MH. Org. Lett.  2003,  5:  1357 

<A NAME="RF07107SS-24">24</A> Parmeintier M. Gros P. Fort Y. Tetrahedron  2005,  61:  3261 

<A NAME="RF07107SS-25">25</A> Kobayashi Y. William AD. Mizojiri R. J. Organomet. Chem.  2002,  653:  91 

<A NAME="RF07107SS-26">26</A> Zhou L. Wang L. Synthesis  2006,  2653 

<A NAME="RF07107SS-27">27</A> Najera C. Gil-Molto J. Karlström S. Falvello LR. Org. Lett.  2003,  5:  1451 

<A NAME="RF07107SS-28">28</A> Ueura K. Satoh T. Miura M. Org. Lett.  2005,  7:  2229