Cross-Coupling Reactions of Aryl Chlorides and Bromides with Phenyl­trimthoxysilane Catalyzed by Palladium-Phosphinous Acid Complexes

Abstract

Three palladium-phosphinous acid complexes, POPd, POPd1, and POPd2, have been employed in cross-coupling reactions of aryl halides and phenyltrimethoxysilane activated by tetrabutylammonium fluoride. A variety of biaryls were prepared from aryl and hetaryl chlorides and bromides in good to high yields under mild reaction conditions. Bromides afford better results than their chloride analogs and acetonitrile was found to be a superior solvent over DMF, ethyl acetate, and isopropyl alcohol. This coupling procedure tolerates nitrile, ketone and ester groups and converts 4,7-dichloroquinoline to 7-chloro-4-phenylquinoline with high regioselectivity.

Key words

cross-coupling reaction - palladium phosphinous acid complexes - phenyltrimethoxysilane - aryl halides - biaryls

References

• 1 For a recent review: Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 
• 2a Meyer G. Rollin Y. Perichon J. Tetrahedron Lett.  1986,  27:  3497 
• 2b Yang SH. Li CS. Cheng CH. J. Org. Chem.  1987,  52:  691 
• 2c Bozell JJ. Vogt CE. J. Am. Chem. Soc.  1988,  110:  2655 
• 2d Merkushev EB. Synthesis  1988,  923 
• 2e Barluenga J. Gonzalez JM. Garcia-Martin MA. Campos PJ. Asensio G. J. Org. Chem.  1993,  58:  2058 
• 2f Milne JE. Jarowicki K. Kocienski PJ. Synlett  2002,  607 
• 2g Schlosser M. Cottet F. Eur. J. Org. Chem.  2002,  4181 
• 2h Klapars A. Buchwald SL. J. Am. Chem. Soc.  2002,  124:  14844 
• 3a Riermeier TH. Zapf A. Beller M. Top. Catal.  1997,  4:  301 
• 3b Shirakawa E. Yamasaki K. Hiyama T. Synthesis  1998,  1544 
• 3c Littke AF. Fu GC. J. Org. Chem.  1999,  64:  10 
• 3d Suzuki A. J. Organomet. Chem.  1999,  576:  147 
• 3e Shiota T. Yamamori T. J. Org. Chem.  1999,  64:  453 
• 3f Littke AF. Fu GC. Angew. Chem., Int. Ed.  1999,  38:  2411 
• 3g Zhang CM. Huang JK. Trudell ML. Nolan ML. J. Org. Chem.  1999,  64:  3804 
• 3h Bei X. Turner HW. Weinberg WH. Tetrahedron Lett.  1999,  40:  3855 
• 3i Bei X. Turner HW. Weinberg WH. Guram AS. J. Org. Chem.  1999,  64:  6797 
• 3j Wolfe JP. Singer RA. Yang BH. Buchwald SL. J. Am. Chem. Soc.  1999,  121:  9550 
• 3k Huang J. Nolan SP. J. Am. Chem. Soc.  1999,  121:  9889 
• 3l Bohm VPW. Herrmann WA. Chem.-Eur. J.  2000,  6:  1017 
• 3m Gruber AS. Zim D. Ebeling G. Monteiro AI. Dupont J. Org. Lett.  2000,  2:  1287 
• 3n Morales-Morales D. Redon R. Yung C. Jensen CM. Chem. Commun.  2000,  1619 
• 3o Bohm VPW. Weskamp T. Gstottmayr CWK. Herrmann WA. Angew. Chem. Int. Ed.  2000,  39:  1602 
• 3p Beletskaya IP. Cheprakov AV. Chem. Rev.  2000,  100:  3009 
• 3q Littke AF. Dai C. Fu GC. J. Am. Chem. Soc.  2000,  122:  4020 
• 3r Zapf A. Ehrentraut A. Beller M. Angew. Chem., Int. Ed.  2000,  39:  4153 
• 3s Stambuli JP. Stauffer SR. Shaughnessy KH. Hartwig JF. J. Am. Chem. Soc.  2001,  123:  2677 
• 3t Dai C. Fu GC. J. Am. Chem. Soc.  2001,  123:  2719 
• 3u Littke AF. Fu GC. J. Am. Chem. Soc.  2001,  123:  6989 
• 3v Whitcombe NJ. Hii KK. Gibson SE. Tetrahedron  2001,  57:  7449 
• 3w Yin JJ. Rainka MP. Zhang XX. Buchwald SL. J. Am. Chem. Soc.  2002,  124:  1162 
• 3x Bedford RB. Cazin CSJ. Hazelwood SL. Chem. Commun.  2002,  2608 
• 3y Bedford RB. Cazin CSJ. Hazelwood SL. Chem. Commun.  2002,  2610 
• 4a Brescia M.-R. DeShong P. J. Org. Chem.  1998,  63:  3156 
• 4b Mowery ME. DeShong P. J. Org. Chem.  1999,  64:  1684 
• 4c Mowery ME. DeShong P. Org. Lett.  1999,  1:  2137 
• 4d DeShong P. Handy CJ. Mowery ME. Pure Appl. Chem.  2000,  72:  1655 
• 4e Correia R. DeShong P. J. Org. Chem.  2001,  66:  7159 
• 4f Hoke ME. Brescia M.-R. Bogaczyk S. DeShong P. King BW. Crimmins MT. J. Org. Chem.  2002,  67:  327 
• 5a Li GY. Angew. Chem., Int. Ed.  2001,  40:  1513 
• 5b Li GY. Zheng G. Noonan AF. J. Org. Chem.  2001,  66:  8677 
• 5c Li GY. J. Org. Chem.  2002,  67:  3643 
• 8 El Sayed K. Al-Said MS. El-Feraly FS. Ross SA. J. Nat. Prod.  2000,  63:  995 
• 9a O’Neill PM. Bray PG. Hawley SR. Ward SA. Park BK. Pharmacol. Ther.  1998,  77:  29 
• 9b Blauer G. Akkawi M. Fleischhacker W. Hiessboeck R. Chirality  1998,  10:  556 
• 9c Egan TJ. Hunter R. Kaschula CH. Marques HM. Misplon A. Walden J. J. Med. Chem.  2000,  43:  283 

6

We observed significant formation of biquinaldine and biphenyl using POPd and POPd2.

7

Employing aryl halides exhibiting nitro, alcohol, phenol or carboxylic acid groups in the POPd1-catalyzed coupling reaction with phenyltrimethoxysilane did not afford the desired products.

10

Replacement of TBAF by CsF resulted in lower yields.