Palladium-Imidazolium N-Heterocyclic Carbene-Catalyzed Carbonylative Amidation With Boronic Acids, Aryl Diazonium Ions, and Ammonia

Yudao Ma; Chun Song; Qiang Chai; Changqin Ma; Merritt B. Andrus

doi:10.1055/s-2003-42478

SPECIALTOPIC

Palladium-Imidazolium N-Heterocyclic Carbene-Catalyzed Carbonylative Amidation With Boronic Acids, Aryl Diazonium Ions, and Ammonia

Yudao Ma^a, Chun Song^b, Qiang Chai^c, Changqin Ma^a, Merritt B. Andrus*^b
^a Chemistry College of Shandong University, Shanda Road #100, Jinan, Shandong 250100, P. R. China
^b Department of Chemistry and Biochemistry, Brigham Young University, C100 BNSN, Provo, Utah 84602, USA
Fax: +(801)4220153; e-Mail: mbandrus@chem.byu.edu;
^c Shandong Academy of Medical Science, Jinan, Shandong 250062, P. R. China

Abstract

All articles of this category

Abstract

Aryl diazonium tetrafluoroborates have been coupled with arylboron compounds, carbon monoxide, and ammonia to give aryl amides in high yields. A saturated N-heterocyclic carbene (NHC) ligand, H₂IPr was used with palladium(II) acetate to give the active catalyst. A mechanism is proposed for this novel four-component coupling reaction.

Key words

palladium cross-coupling - multi-component - carbonylative coupling - amides - N-heterocyclic carbene

Full Text

References

<A NAME="RC14003SS-1A">1a</A> Ritter K. Synthesis 1993, 735

<A NAME="RC14003SS-1B">1b</A> Schoenberg A. Bartoletti I. Heck RF. J. Org. Chem. 1974, 39: 3318

<A NAME="RC14003SS-1C">1c</A> Schoenberg A. Heck RF. J. Org. Chem. 1974, 39: 3327

<A NAME="RC14003SS-1D">1d</A> Gaviño R. Pellegrini S. Castenet Y. Mortreux A. Mentre O. Appl. Catal. A 2001, 217: 91

<A NAME="RC14003SS-2A">2a</A> Echavarren AM. Stille JK. J. Am. Chem. Soc. 1988, 110: 1557

<A NAME="RC14003SS-2B">2b</A> Ceccarelli S. Piarulli U. Gennari C. J. Org. Chem. 2000, 65: 6254

<A NAME="RC14003SS-3A">3a</A> Ishiyama T. Kizaki H. Suzuki A. Miyaura N. Tetrahedron Lett. 1993, 34: 7595

<A NAME="RC14003SS-3B">3b</A> Ishiyama T. Kizaki H. Hayashi T. Suzuki A. Miyaura N. J. Org. Chem. 1998, 63: 4726

<A NAME="RC14003SS-3C">3c</A> Skoda-Földes R. Székvölgi Z. Kollár L. Berente Z. Horváth J. Tuba Z. Tetrahedron 2000, 56: 3415

<A NAME="RC14003SS-4">4</A> Iwata T. Miyake Y. Nishibayashi Y. Uemura S. J. Chem. Soc., Perkin Trans. 1 2002, 1548

<A NAME="RC14003SS-5">5</A> Yamamoto M. Kohara T. Yamamoto A. Chem. Lett. 1976, 1217

<A NAME="RC14003SS-6">6</A> Bumagin NA. Ponomaryov AB. Beletskaya IP. Tetrahedron Lett. 1985, 26: 4819

<A NAME="RC14003SS-7">7</A> Hatanaka Y. Fukushima S. Hiyama T. Tetrahedron 1992, 48: 2113

<A NAME="RC14003SS-8A">8a</A> Kang S.-K. Kim W.-Y. Lee Y.-T. Ahn S.-K. Kim J.-C. Tetrahedron Lett. 1998, 39: 2131

<A NAME="RC14003SS-8B">8b</A> Kang S.-K. Lim K.-H. Ho P.-S. Yoon S.-K. Son H.-J. Synth. Commun. 1998, 28: 1481

<A NAME="RC14003SS-9A">9a</A> Beletskaya IP. Cheprakov AV. Chem. Rev. 2000, 100: 3009

<A NAME="RC14003SS-9B">9b</A> Hua DH. Takasu K. Huang X. Millward GS. Chen Y. Fan J. Tetrahedron 2000, 56: 7389

<A NAME="RC14003SS-10A">10a</A> Negishi E.-i. Copéret C. Ma S. Liou S.-Y. Liu F. Chem. Rev. 1996, 96: 365

<A NAME="RC14003SS-10B">10b</A> Dai G. Larock RC. J. Org. Chem. 2002, 67: 7042

<A NAME="RC14003SS-11A">11a</A> Tanaka M. Kobayashi T. Sakakura T. J. Chem. Soc. Jpn. 1985, 537

<A NAME="RC14003SS-11B">11b</A> Kiji J. Okano T. Kimura H. Saiki K. J. Mol. Catal. A: Chem. 1998, 130: 95

<A NAME="RC14003SS-12">12</A> Nishiyama Y. Tokunaga K. Kawamatsu H. Sonoda N. Tetrahedron Lett. 2002, 43: 1507

<A NAME="RC14003SS-13A">13a</A> Grushin VV. Alper H. Chem. Rev. 1994, 94: 1047

<A NAME="RC14003SS-13B">13b</A> Georgsson J. Hallberg A. Larhed M. J. Comb. Chem. 2003, 5: 350

<A NAME="RC14003SS-14">14</A> Carpentier J.-F. Castanet Y. Brocard J. Mortreux A. Petit F. Tetrahedron Lett. 1991, 32: 4705

<A NAME="RC14003SS-15">15</A> Morimoto T. Fujioka M. Fuji K. Tsutsumi K. Kakiuchi K. Chem. Lett. 2003, 32: 154

<A NAME="RC14003SS-16">16</A> Andrus MB. Ma Y. Zang Y. Song C. Tetrahedron Lett. 2002, 43: 9137

<A NAME="RC14003SS-17A">17a</A> Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290

<A NAME="RC14003SS-17B">17b</A> Herrmann WA. Kocher C. Angew. Chem., Int. Ed. Engl. 1997, 36: 2162

<A NAME="RC14003SS-18A">18a</A> Herrmann WA. Elison M. Fischer J. Kocher C. Artus GRJ. Angew. Chem., Int. Ed. Engl. 1995, 34: 2371

<A NAME="RC14003SS-18B">18b</A> Yang C. Lee HM. Nolan SP. Org. Lett. 2001, 3: 1511

<A NAME="RC14003SS-19A">19a</A> Zhang C. Huang J. Trudell ML. Nolan SP. J. Org. Chem. 1999, 64: 3804

<A NAME="RC14003SS-19B">19b</A> Fürstner A. Leitner A. Synlett 2001, 290

<A NAME="RC14003SS-19C">19c</A> Grasa GA. Hillier AC. Nolan SP. Org. Lett. 2001, 3: 1077

<A NAME="RC14003SS-20">20</A> Lee HM. Nolan SP. Org. Lett. 2000, 2: 2053

<A NAME="RC14003SS-21A">21a</A> Huang J. Nolan SP. J. Am. Chem. Soc. 1999, 121: 9889

<A NAME="RC14003SS-21B">21b</A> Bölm VPW. Weskamp T. Gstöttmayr CWK. Herrman WA. Angew. Chem. Int. Ed. 2000, 39: 1602

<A NAME="RC14003SS-22A">22a</A> Andrus MB. Song C. Org. Lett. 2001, 3: 3761

<A NAME="RC14003SS-22B">22b</A> Andrus MB. Song C. Zhang J. Org. Lett. 2002, 4: 2079

<A NAME="RC14003SS-22C">22c</A> Ma Y. Song C. Jiang W. Xue G. Cannon JF. Wang X. Andrus MB. Org. Lett. 2003, in press