A Practical and Efficient Synthesis of 5′-Substituted m-Terphenyls

Joanne D. Kehlbeck; Eric J. Dimise; Sarah M. Sparks; Skylar Ferrara; Joseph M. Tanski; Craig M. Anderson

doi:10.1055/s-2007-983722

PAPER

A Practical and Efficient Synthesis of 5′-Substituted m-Terphenyls

Joanne D. Kehlbeck^a, Eric J. Dimise^a, Sarah M. Sparks^a, Skylar Ferrara^c, Joseph M. Tanski^b, Craig M. Anderson*^c
^a Department of Chemistry, Union College, Schenectady, NY 12308, USA
^b Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA
^c Department of Chemistry, Bard College, Annandale-on-Hudson, NY 12504, USA
Fax: +1(845)7587628; e-Mail: canderso@bard.edu;

Abstract

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Abstract

Outlined is a simple, convenient, scalable procedure for the synthesis of a variety of 5′-substituted m-terphenyl compounds from commercially available materials. A series of novel compounds were generated based on the m-terphenyl scaffold. In addition we present a full and complete characterization, including the crystal structure, of 3,5-diphenylbenzaldehyde (1,1′:3′,1′′-terphenyl-5′-carbaldehyde).

Key words

imine - Kumada - pyridine - heterocycle - biaryl

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References

References.

<A NAME="RM01407SS-1">1</A> Liu J.-K. Chem. Rev. 2006, 106: 2209

<A NAME="RM01407SS-2A">2a</A> Simoni D. Giannini G. Roberti M. Rondanin R. Baruchello R. Rossi M. Grisolia G. Invidiata FP. Aiello S. Marino S. Cavallini S. Siniscalchi A. Gebbia N. Crosta L. Grimaudo S. Abbadessa V. DiCristina A. Tolomeo M. J. Med. Chem. 2005, 48: 4293

<A NAME="RM01407SS-2B">2b</A> Greenfield AA. Butera JA. Caufield CE. Tetrahedron Lett. 2003, 44: 2729

<A NAME="RM01407SS-3">3</A> Goto K. Yamamoto G. Tan B. Okazaki R. Tetrahedron Lett. 2001, 42: 4875

<A NAME="RM01407SS-4A">4a</A> Inada Y. Nishibayashi Y. Uemura S. Angew. Chem. Int. Ed. 2005, 44: 7715

<A NAME="RM01407SS-4B">4b</A> Luning U. Baumgartner H. Manthey C. Meynhardt B. J. Org. Chem. 1996, 61: 7922

<A NAME="RM01407SS-4C">4c</A> Rabe GW. Zhang-Presse M. Reiderer FA. Golen JA. Incarvito CD. Rheingold AL. Inorg. Chem. 2003, 42: 7587

<A NAME="RM01407SS-5A">5a</A> Fang Y. Hanan GS. Synlett 2003, 852

<A NAME="RM01407SS-5B">5b</A> Wang J. Hanan GS. Synlett 2005, 1251

<A NAME="RM01407SS-5C">5c</A> Shi J, Chen CH, and Klubek KP. inventors; US 5,972,247.

<A NAME="RM01407SS-5D">5d</A> Dickie DA. Schatte G. Jennings MC. Jenkins HA. Khoo SYL. Clyburne JAC. Inorg. Chem. 2006, 45: 1646

<A NAME="RM01407SS-5E">5e</A> Rajakumar P. Srinivasan K. Tetrahedron 2004, 60: 10285

<A NAME="RM01407SS-5F">5f</A> Riddle JA. Lathrop SP. Bollinger JC. Lee D. J. Am. Chem. Soc. 2006, 128: 10986

<A NAME="RM01407SS-6">6</A> Du CJF. Hart H. Ng KKD. J. Org. Chem. 1986, 51: 3162

<A NAME="RM01407SS-7">7</A> Olah GA. Ohannesian L. Arvanaghi M. J. Org. Chem. 1984, 49: 3856

<A NAME="RM01407SS-8">8</A> Ohemeng KA, and Nguyen VN. inventors; US 5,942,532.

Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Gaussian Inc.: Wallingford, CT, 2004.

Spartan 04, Wavefunction Inc.: Irvine, CA, 2004.

<A NAME="RM01407SS-11">11</A> Leazer JL. Cvetovich R. Tsay FR. Dolling U. Vickery T. Bachert D. J. Org. Chem. 2003, 68: 3695

<A NAME="RM01407SS-12">12</A> Bohm VPW. Weskamp T. Gstottmayr CWK. Herrmann WA. Angew. Chem. Int. Ed. 2000, 39: 1602

<A NAME="RM01407SS-13A">13a</A> Bolton R. Sandall JPB. J. Chem. Soc., Perkin Trans. 2 1977, 278

<A NAME="RM01407SS-13B">13b</A> Barbero M. Degani I. Diulgheroff N. Dughera S. Fochi R. Synthesis 2001, 2180

CCDC 616026 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Rd, Cambridge CB2 1EZ, UK; fax: +44(1223)336033.

Sheldrick, G. M. SHELXTL, An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data, University of Göttingen: Göttingen, Germany, 1981.