A Novel Stereoselective Synthesis of Symmetrical (1E,3E)-1,4-Diarylbuta-1,3-dienes

Francesco Babudri; Gianluca M. Farinola; Francesco Naso; Roberta Ragni; Giulia Spina

doi:10.1055/s-2007-983833

PSP

A Novel Stereoselective Synthesis of Symmetrical (1E,3E)-1,4-Diarylbuta-1,3-dienes

Francesco Babudri^a,b, Gianluca M. Farinola*^a, Francesco Naso^a,b, Roberta Ragni^a, Giulia Spina^a
^a Dipartimento di Chimica, Università degli Studi di Bari, via Orabona 4, 70126 Bari, Italy
Fax: +39(80)5442129; e-Mail: farinola@chimica.uniba.it;
^b CNR ICCOM Bari, Dipartimento di Chimica, Università degli Studi di Bari, via Orabona 4, 70126 Bari, Italy

Abstract

All articles of this category

Abstract

A convenient methodology for the stereoselective synthesis of symmetrical (1E,3E)-1,4-diarylbuta-1,3-dienes based on palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of (1E,3E)-1,4-diiodobuta-1,3-diene with arylboronic reagents is reported.

Key words

diene - Suzuki cross-coupling reaction - stereoselective synthesis - palladium

Full Text

References

<A NAME="RZ06007ST-1">1</A> Mori K. The Synthesis of Insect Pheromones, In The Total Synthesis of Natural Products Vol. 4: ApSimon J. John Wiley and Sons; New York: 1981.

<A NAME="RZ06007ST-2">2</A> Singh AK. Darshi M. Kanvah S. J. Phys. Chem. A 2000, 104: 464

<A NAME="RZ06007ST-3">3</A> Adachi C. Tsutsui T. Saito S. Appl. Phys. Lett. 1990, 56: 799

<A NAME="RZ06007ST-4A">4a</A> Kanis DR. Ratner MA. Marks TJ. Chem. Rev. 1994, 94: 195

<A NAME="RZ06007ST-4B">4b</A> Mladenova M. Ventelon L. Blanchard-Desche M. Tetrahedron Lett. 1999, 40: 6923

<A NAME="RZ06007ST-5">5</A> Fringuelli F. Taticchi A. Dienes in the Diels-Alder Reaction John Wiley and Sons; New York: 1990.

<A NAME="RZ06007ST-6A">6a</A> Okukado N. Uchikawa O. Nakamura Y. Chem. Lett. 1988, 1449

<A NAME="RZ06007ST-6B">6b</A> Ideses R. Shani A. Tetrahedron 1989, 45: 3523

<A NAME="RZ06007ST-6C">6c</A> Benahmed-Gasmi A. Frère P. Elandaloussi EH. Roncali J. Orduna J. Garin J. Jubault M. Riou A. Gorgues A. Chem. Mater. 1996, 8: 2291

<A NAME="RZ06007ST-6D">6d</A> Frère P. Raimundo JM. Blanchard P. Delaunay J. Richomme P. Sauvajol JL. Orduna J. Garin J. Roncali J. J. Org. Chem. 2003, 68: 7254

<A NAME="RZ06007ST-7A">7a</A> Patro B. Ila H. Junjappa H. Tetrahedron Lett. 1992, 33: 809

<A NAME="RZ06007ST-7B">7b</A> Yu CC. Ng DKP. Chen B.-L. Luh T.-Y. Organometallics 1994, 13: 1487

<A NAME="RZ06007ST-7C">7c</A> Ranu BC. Banerjee S. Eur. J. Org. Chem. 2006, 3012

<A NAME="RZ06007ST-8A">8a</A> Diver ST. Giessert AJ. Synthesis 2003, 466

<A NAME="RZ06007ST-8B">8b</A> Diver ST. Giessert AJ. Chem. Rev. 2004, 104: 1317

<A NAME="RZ06007ST-9A">9a</A> Paventi M. Hay AS. Synthesis 1990, 878

<A NAME="RZ06007ST-9B">9b</A> Wang SJ. Tjong SC. Meng YZ. Fung MK. Lee ST. Hay AS. J. Appl. Polym. Sci. 2003, 89: 1645

<A NAME="RZ06007ST-10">10</A> Metal-Catalyzed Cross-Coupling Reactions 2nd ed.: de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004.

<A NAME="RZ06007ST-11A">11a</A> Kanemoto S. Matsubara S. Oshima K. Utimoto K. Nozaki H. Chem. Lett. 1987, 5

<A NAME="RZ06007ST-11B">11b</A> Kang S.-K. Namkoong E.-Y. Yamaguchi T. Synth. Commun. 1997, 27: 641

<A NAME="RZ06007ST-11C">11c</A> Alcaraz L. Taylor RJK. Synlett 1997, 791

<A NAME="RZ06007ST-12A">12a</A> Ramana Rao VV. Vijaya Kumar Ch. Devaprabhakara D. J. Organomet. Chem. 1979, 179: C7

<A NAME="RZ06007ST-12B">12b</A> Parrish JP. Jung YC. Floyd RJ. Woon Jung K. Tetrahedron Lett. 2002, 43: 7899

<A NAME="RZ06007ST-12C">12c</A> Kabalka GW. Wang L. Tetrahedron Lett. 2002, 43: 3067

<A NAME="RZ06007ST-13A">13a</A> Tamao K. Matsumoto H. Kakui T. Kumada M. Tetrahedron Lett. 1979, 20: 1137

<A NAME="RZ06007ST-13B">13b</A> Itami K. Ushiogi Y. Nokami T. Ohashi Y. Yoshida J.-i. Org. Lett. 2004, 6: 3695

<A NAME="RZ06007ST-14A">14a</A> Tanaka H. Kosaka A. Yamashita S. Morisaki K. Torii S. Tetrahedron Lett. 1989, 30: 1261

<A NAME="RZ06007ST-14B">14b</A> Lee PH. Seomoon D. Lee K. Org. Lett. 2005, 7: 343

<A NAME="RZ06007ST-15A">15a</A> Miyaura N. Yamada K. Suginome H. Suzuki A. J. Am. Chem. Soc. 1985, 107: 972

<A NAME="RZ06007ST-15B">15b</A> Kobayashi Y. William AD. Org. Lett. 2002, 4: 4241

<A NAME="RZ06007ST-15C">15c</A> Takagi J. Takahashi K. Ishiyama T. Miyaura N. J. Am. Chem. Soc. 2002, 124: 8001

<A NAME="RZ06007ST-15D">15d</A> Molander GA. Felix LA. J. Org. Chem. 2005, 70: 3950

<A NAME="RZ06007ST-15E">15e</A> Suzuki A. Chem. Commun. 2005, 4759

<A NAME="RZ06007ST-15F">15f</A> Alami M. Peyrat J.-F. Brion J.-D. Tetrahedron Lett. 2002, 43: 3007

<A NAME="RZ06007ST-16">16</A> Stille JK. Groh BL. J. Am. Chem. Soc. 1987, 109: 813

<A NAME="RZ06007ST-17A">17a</A> Tucker CE. Majid TN. Knochel P. J. Am. Chem. Soc. 1992, 114: 3983

<A NAME="RZ06007ST-17B">17b</A> Zeng X. Qian M. Hu Q. Negishi E.-i. Angew. Chem. Int. Ed. 2004, 43: 2259

<A NAME="RZ06007ST-18">18</A> Wang Z. Wnuk SF. J. Org. Chem. 2005, 70: 3281

<A NAME="RZ06007ST-19A">19a</A> Cai M. Ye H. Zhao H. Song C. J. Organomet. Chem. 2003, 687: 462

<A NAME="RZ06007ST-19B">19b</A> Cai M.-Z. Ye X.-L. Wang P.-P. Synthesis 2005, 2654

<A NAME="RZ06007ST-20">20</A> Fiandanese V. Marchese G. Mascolo G. Naso F. Ronzini L. Tetrahedron Lett. 1988, 29: 3705

<A NAME="RZ06007ST-21">21</A> Ikeda Z. Oshima K. Matsubara S. Org. Lett. 2005, 7: 4859

<A NAME="RZ06007ST-22A">22a</A> Babudri F. Farinola GM. Fiandanese V. Mazzone L. Naso F. Tetrahedron 1998, 54: 1085

<A NAME="RZ06007ST-22B">22b</A> Denmark SE. Tymonko SA. J. Am. Chem. Soc. 2005, 127: 8004

<A NAME="RZ06007ST-23">23</A> Coleman RS. Walczak MC. Org. Lett. 2005, 7: 2289

<A NAME="RZ06007ST-24A">24a</A> Babudri F. Fiandanese V. Naso F. J. Org. Chem. 1991, 56: 6245

<A NAME="RZ06007ST-24B">24b</A> Babudri F. Cicciomessere AR. Farinola GM. Fiandanese V. Marchese G. Musio R. Naso F. Sciacovelli O. J. Org. Chem. 1997, 62: 3291

<A NAME="RZ06007ST-25">25</A> Yamamoto T. Yasuda T. Kobayashi K. Yamaguchi I. Koizumi T.-a. Ishii D. Nakagawa M. Mashiko Y. Shimizu N. Bull. Chem. Soc. Jpn. 2006, 79: 498

<A NAME="RZ06007ST-26">26</A> Trostyanskaya IG. Titskiy DY. Anufrieva EA. Borisenko AA. Kazankova MA. Beletskaya IP. Russ. Chem. Bull., Int. Ed. 2001, 50: 2095

<A NAME="RZ06007ST-27">27</A> Babudri F. Fiandanese V. Mazzone L. Naso F. Tetrahedron Lett. 1994, 35: 8847

For some recent reviews see:

<A NAME="RZ06007ST-28A">28a</A> Babudri F. Farinola GM. Naso F. J. Mater. Chem. 2004, 14: 11

<A NAME="RZ06007ST-28B">28b</A> Babudri F. Farinola GM. Naso F. Ragni R. Chem. Commun. 2007, 1003

<A NAME="RZ06007ST-29A">29a</A> Mitchenko SA. Ananikov VP. Beletskaya IP. Ustynyuk YA. Mendeleev Commun. 1997, 130

<A NAME="RZ06007ST-29B">29b</A> Mitchenko SA. Kinet. Catal. 1999, 40: 253

<A NAME="RZ06007ST-29C">29c</A> Ananikov VP. Musaev DG. Morokuma K. Organometallics 2001, 20: 1652

<A NAME="RZ06007ST-29D">29d</A> Ananikov VP. Mitchenko SA. Beletskaya IP. Russ. J. Org. Chem. (Engl. Transl.) 2002, 38: 636

<A NAME="RZ06007ST-30">30</A> Kielh A. Eberhardt A. Müllen K. Liebigs Ann. Chem. 1995, 223

<A NAME="RZ06007ST-31">31</A> Ashe AJ. Drone FJ. Organometallics 1985, 4: 1478

<A NAME="RZ06007ST-32">32</A> Ferede R. Noble M. Cordes AW. Allison NT. Lay J. J. Organomet. Chem. 1988, 339: 1