Boron Trihalide Mediated Haloallylation
of Aryl Aldehydes and Its Application to the Preparation
of (E)-1,3-Dienes

Michael P. Quinn; Min-Liang Yao; Li Yong; George W. Kabalka

doi:10.1055/s-0031-1289304

PAPER

Boron Trihalide Mediated Haloallylation of Aryl Aldehydes and Its Application to the Preparation of (E)-1,3-Dienes

Michael P. Quinn, Min-Liang Yao, Li Yong, George W. Kabalka*
Departments of Chemistry and Radiology, The University of Tennessee, Knoxville, TN 37996-1600, USA
Fax: +1(865)9742997; e-Mail: kabalka@utk.edu;

Abstract

Alle Artikel dieser Rubrik

Abstract

In the presence of boron trihalides, aryl aldehydes couple readily with allylmetals to afford haloallylated products. The reactions tolerate a variety of functional groups. Simple aqueous workup of haloallylation reactions, followed by treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene, provides a straightforward route to synthetically useful (E)-1,3-dienes. The mild reaction conditions, readily available starting materials, and high stereoselectivity make this two-step (E)-1,3-diene synthesis quite attractive.

Key words

boron trihalide - allylmetal - haloallylation - diene - stereoselectivity

Volltext

Referenzen

References

<A NAME="RM81011SS-1A">1a</A> Bhatt MV. Kalkarni SU. Synthesis 1983, 249

<A NAME="RM81011SS-1B">1b</A> Desvergnes S. Vallée Y. Py S. Org. Lett. 2008, 10: 2967

<A NAME="RM81011SS-1C">1c</A> Nguyen NH. Cougnon C. Gohier F. J. Org. Chem. 2009, 74: 3955

<A NAME="RM81011SS-1D">1d</A> Yao M.-L. Reddy MS. Zeng W.-B. Hall K. Walfish I. Kabalka GW. J. Org. Chem. 2009, 74: 1385 ; and references cited therein

<A NAME="RM81011SS-2">2</A> Sprott KT. Corey EJ. Org. Lett. 2003, 5: 2465

<A NAME="RM81011SS-3">3</A> Lappert MF. Prokai B. J. Organomet. Chem. 1964, 1: 384

<A NAME="RM81011SS-4A">4a</A> Suzuki A. Pure Appl. Chem. 1986, 58: 629 ; and references cited therein

<A NAME="RM81011SS-4B">4b</A> Wang KK. Wang Z. Tarli A. Gannett P. J. Am. Chem. Soc. 1996, 118: 10783

<A NAME="RM81011SS-4C">4c</A> Yao M.-L. Reddy MS. Yong L. Walfish I. Blevins DW. Kabalka GW. Org. Lett. 2010, 12: 700

<A NAME="RM81011SS-4D">4d</A> Wang C. Tobrman T. Xu Z. Negishi E.-i. Org. Lett. 2009, 11: 4092

<A NAME="RM81011SS-4E">4e</A> Lee SJ. Gray KC. Paek JS. Burke MD.
J. Am. Chem. Soc. 2008, 130: 466

<A NAME="RM81011SS-5">5</A> Amrollah-Madjdababi A. Pham TN. Ashby EC. Synthesis 1989, 614

<A NAME="RM81011SS-6A">6a</A> Parker DL. Fried AK. Meng D. Greenlee ML. Org. Lett. 2008, 10: 2983

<A NAME="RM81011SS-6B">6b</A> Goldstein M. Haines LIB. Hemmings JAG. J. Chem. Soc., Dalton Trans. 1972, 2260

<A NAME="RM81011SS-6C">6c</A> Namavari M. Satyamurthy N. Barrio JR.
J. Fluorine Chem. 1995, 72: 89

<A NAME="RM81011SS-7">7</A> Rabinovitz M. Grinvald A. J. Am. Chem. Soc. 1972, 94: 2724

<A NAME="RM81011SS-8">8</A> Nakamura E. Yamanaka M. Mori S. J. Am. Chem. Soc. 2000, 122: 1826

<A NAME="RM81011SS-9">9</A> Frazer MJ. Gerrard W. Lappert MF. J. Chem. Soc. 1957, 739

<A NAME="RM81011SS-10A">10a</A> Kabalka GW. Wu Z. Tetrahedron Lett. 2000, 41: 579

<A NAME="RM81011SS-10B">10b</A> Lansinger JM. Ronald RC. Synth. Commun. 1979, 9: 341

<A NAME="RM81011SS-11A">11a</A> Kabalka GW. Wu Z. Ju Y. Tetrahedron Lett. 2001, 42: 5793

<A NAME="RM81011SS-11B">11b</A> Kabalka GW. Wu Z. Ju Y. Synthesis 2004, 2927

<A NAME="RM81011SS-11C">11c</A> Kabalka GW. Wu Z. Ju Y. Yao M.-L. J. Org. Chem. 2005, 70: 10285

<A NAME="RM81011SS-12A">12a</A> Kabalka GW. Wu Z. Ju Y. Org. Lett. 2002, 4: 1491

<A NAME="RM81011SS-12B">12b</A> Kabalka GW. Yao M.-L. Borella S. Wu Z. Ju Y. J. Org. Chem. 2008, 73: 2668

<A NAME="RM81011SS-12C">12c</A> Yao M.-L. Quinn MP. Kabalka GW. Heterocycles 2010, 80: 779

<A NAME="RM81011SS-13A">13a</A> Kabalka GW. Yao M.-L. Borella S. Wu Z. Chem. Commun. 2005, 2492

<A NAME="RM81011SS-13B">13b</A> Kabalka GW. Yao M.-L. Borella S. Wu Z. Org. Lett. 2005, 7: 2865

<A NAME="RM81011SS-14">14</A> Kabalka GW. Yao M.-L. Borella S. J. Am. Chem. Soc. 2006, 128: 11320

<A NAME="RM81011SS-15">15</A> Yao M.-L. Borella S. Quick T. Kabalka GW. J. Chem. Soc., Dalton Trans. 2008, 776

<A NAME="RM81011SS-16">16</A> Mayr H. Gorath G. J. Am. Chem. Soc. 1995, 117: 7862

<A NAME="RM81011SS-17A">17a</A> Mundal DA. Lutz KE. Thomson RJ. Org. Lett. 2009, 11: 465

<A NAME="RM81011SS-17B">17b</A> Mundal DA. Lee JJ. Thomson RJ. J. Am. Chem. Soc. 2008, 130: 1148

<A NAME="RM81011SS-17C">17c</A> Siebert MR. Tantillo DJ. Org. Lett. 2008, 10: 3219

<A NAME="RM81011SS-18">18</A> Meriºor E. Conrad J. Malakar CC. Beifuss U. Synlett 2008, 903

<A NAME="RM81011SS-19">19</A> Denmark SC. Fu J. Chem. Rev. 2003, 103: 2763 ; and references cited therein

<A NAME="RM81011SS-20">20</A> Han A.-R. Kim M.-S. Jeong YH. Lee SK. Seo E.-K. Chem. Pharm. Bull. 2005, 53: 1466

<A NAME="RM81011SS-21">21</A> Pereira AR. Cabezas JA. J. Org. Chem. 2005, 70: 2594

<A NAME="RM81011SS-22">22</A> Moreira JA. McElfresh JS. Millar JG. J. Chem. Ecol. 2006, 32: 169

<A NAME="RM81011SS-23">23</A> Roege KE. Kelly WL. Org. Lett. 2009, 11: 297

<A NAME="RM81011SS-24A">24a</A> Nicolaou KG. Snyder SS. Montagnon T. Vassilikogianakis G. Angew. Chem. Int. Ed. 2002, 41: 1668

<A NAME="RM81011SS-24B">24b</A> Brieger G. Bennett JN. Chem. Rev. 1980, 80: 63

<A NAME="RM81011SS-25">25</A> Nakao Y. Idei H. Kanyiva KS. Hiyama T. J. Am. Chem. Soc. 2009, 131: 5070

<A NAME="RM81011SS-26">26</A> Watkins AL. Landis CR. Org. Lett. 2011, 13: 164

<A NAME="RM81011SS-27A">27a</A> Friebe L. Nuyken O. Obrecht W. Adv. Polym. Sci. 2006, 204: 1

<A NAME="RM81011SS-27B">27b</A> Fischbach AA. Anwander R. Adv. Polym. Sci. 2006, 204: 155

<A NAME="RM81011SS-27C">27c</A> Proto A. Capacchione C. In Stereoselective Polymerization with Single-Site Catalysts Baugh LS. Canich LAM. CRC Press; Boca Raton: 2008. p.447

<A NAME="RM81011SS-28A">28a</A> Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4442

<A NAME="RM81011SS-28B">28b</A> Molander GA. Yokoyama Y. J. Org. Chem. 2006, 71: 2493

<A NAME="RM81011SS-28C">28c</A> Smith CR. RajanBabu TV. Tetrahedron 2010, 66: 1102

<A NAME="RM81011SS-29A">29a</A> Zhou R. Wang C. Song H. He Z. Org. Lett. 2010, 12: 976

<A NAME="RM81011SS-29B">29b</A> McNulty J. Das P. Tetrahedron Lett. 2009, 50: 5737

<A NAME="RM81011SS-30">30</A> Date SM. Ghosh SK. Angew. Chem. Int. Ed. 2007, 46: 386

<A NAME="RM81011SS-31">31</A> Cuvigny T. Hervé du Penhoat C. Julia M. Tetrahedron Lett. 1983, 24: 4315

<A NAME="RM81011SS-32">32</A> Al-Badri H. About-Jaudet E. Collignon N. Tetrahedron Lett. 1996, 37: 2951

<A NAME="RM81011SS-33">33</A> Oriyama T. Iwanami K. Tsukamoto K. Ichimura Y. Koga G. Bull. Chem. Soc. Jpn. 1991, 64: 1410

<A NAME="RM81011SS-34">34</A> Padwa A. Kulkarni YS. Terry LW. J. Org. Chem. 1990, 55: 2478

<A NAME="RM81011SS-35">35</A> Gu X. Ndungu JM. Qiu W. Ying J. Carducci MD. Wooden H. Hruby VJ. Tetrahedron 2004, 60: 8233

<A NAME="RM81011SS-36">36</A> Macreadie IG. Avery TD. Robinson TV. Macreadie P. Barraclough M. Taylor DK. Tiekink ERT. Tetrahedron 2008, 64: 1225

<A NAME="RM81011SS-37">37</A> Mitsudo T. Fischetti W. Heck RF. J. Org. Chem. 1984, 49: 1640

Zusatzmaterial

Supporting Information (PDF) (opens in new window)