Disubstituted Benzenes from
Acyclic Precursors by a [5+1] Annulation

David S. B. Daniels; John M. Brown; Maud Gayral; Yingjian Xu; Malcolm I. Stewart

doi:10.1055/s-0029-1217162

LETTER

Disubstituted Benzenes from Acyclic Precursors by a [5+1] Annulation

David S. B. Daniels, John M. Brown, Maud Gayral, Yingjian Xu, Malcolm I. Stewart*
Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK
Fax: +44(1865)285002; e-Mail: malcolm.stewart@chem.ox.ac.uk;

Abstract

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Abstract

Horner-Wadsworth-Emmons reaction of stannylvinylphosphonates with aldehydes and mild thermal cyclisation provides disubstituted arylstannanes. Subsequent Stille coupling leads to regiospecific synthesis of m- and p-terphenyls.

Key words

Horner-Wadsworth-Emmons - Palladium coupling arylstannanes - Stille reaction - terphenyls

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References

<A NAME="RD02909ST-1A">1a</A> Doherty S. Knight JG. Smyth CH. Harrington RW. Clegg W. Org. Lett. 2007, 9: 4925

<A NAME="RD02909ST-1B">1b</A> Suda T. Noguchi K. Hirano M. Tanaka K. Chem. Eur. J. 2008, 14: 6593

<A NAME="RD02909ST-2A">2a</A> Ashburn BO. Carter RG. Zakharov LN. J. Org. Chem. 2008, 73: 7305

<A NAME="RD02909ST-2B">2b</A> For a review, see: Harrity JPA. Tetrahedron 2007, 64: 767

<A NAME="RD02909ST-2C">2c</A> Shibata T. Fujiwara R. Takano D. Synlett 2007, 2766 ; and references cited therein

<A NAME="RD02909ST-3A">3a</A> Yoshida K. Narui R. Imamoto T. Chem. Eur. J. 2008, 14: 9706

<A NAME="RD02909ST-3B">3b</A> Yoshida K. Takahashi H. Imamoto T. Chem. Eur. J. 2008, 14: 8246

<A NAME="RD02909ST-4A">4a</A> Hefner J. Langer P. Tetrahedron Lett. 2008, 49: 4470

<A NAME="RD02909ST-4B">4b</A> Fatusin O. Shkoor M. Riahi A. Reinke H. Langer P. Synlett 2009, 201

<A NAME="RD02909ST-5">5</A> Bi XH. Dong DW. Liu Q. Pan W. Zhao L. Li B. J. Am. Chem. Soc. 2005, 127: 4578

<A NAME="RD02909ST-6">6</A> Gayral M. Brown JM. Synlett 2007, 2823

<A NAME="RD02909ST-7">7</A> Chemin DG. Linstrumelle G. Tetrahedron 1994, 50: 5335

<A NAME="RD02909ST-8">8</A> Mole SJ. Zhou X. Liu R. J. Phys. Chem. 1996, 100: 14665

<A NAME="RD02909ST-9">9</A> Hamze A. Provot O. Brion JD. Alami M. J. Org. Chem. 2007, 72: 3868

<A NAME="RD02909ST-10A">10a</A> Littke AF. Schwarz L. Fu GC. J. Am. Chem. Soc. 2002, 124: 6343

<A NAME="RD02909ST-10B">10b</A> Netherton MR. Fu GC. Org. Lett. 2001, 3: 4295

<A NAME="RD02909ST-11">11</A> Hii KK. Antelo Miguez JM. Adrio LA. Sousa-Pedrares A. Vila JM. J. Org. Chem. 2007, 72: 7771