Solventless Suzuki Coupling Reactions On Palladium-Doped Potassium Fluoride­ Alumina

George W.  Kabalka; Lei  Wang; Richard M.  Pagni; C. Maxwell  Hair; Vasudevan  Namboodiri

doi:10.1055/s-2003-36821

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Synthesis 2003(2): 0217-0222
DOI: 10.1055/s-2003-36821

PAPER

Solventless Suzuki Coupling Reactions On Palladium-Doped Potassium Fluoride Alumina

George W. Kabalka*, Lei Wang, Richard M. Pagni, C. Maxwell Hair, Vasudevan Namboodiri
Departments of Chemistry and Radiology, The University of Tennessee, Knoxville, TN 37996-1600, USA
Fax: +1(865)9742997; e-Mail: kabalka@utk.edu;

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Publication History

Received 23 January 2002
Publication Date:
22 January 2003 (online)

Abstract
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Abstract

A solventless Suzuki coupling reaction has been developed which utilizes a commercially available potassium fluoride alumina mixture and palladium powder. The new reaction is convenient, environmentally friendly, and generates good yields of the coupled products. Aryl iodides react faster than the bromides or chlorides; aryl groups are also more reactive than alkenyl groups, which react faster than alkyl groups. The use of microwave irradiation accelerates the reaction, decreasing reaction times from hours to minutes. The palladium powder catalyst can be recycled using a simple filtration and washing sequence without loss of catalytic activity.

Key words

Suzuki reactions - coupling - boron - alumina - green chemistry - microwave irradiation - substituent effects

References

1a Tamao K. Kiso Y. Sumitani K. Kumada M. J. Am. Chem. Soc. 1972, 94: 9268

Crossref Google Scholar
1b Hayashi T. Konishi M. Kobori Y. Kumada M. Higuchi T. Hirotsu K. J. Am. Chem. Soc. 1984, 106: 158

Crossref Google Scholar
2 Corriu R. Masse JP. J. Chem. Soc., Chem. Commun. 1972, 144

Google Scholar
3 Yamamura M. Moritani I. Murahashi S. J. Organomet. Chem. 1975, 23: C39

Google Scholar
4a Negishi E. Takahashi T. Baba S. Van Horn DE. Okukado N. J. Am. Chem. Soc. 1987, 109: 2393

Crossref Google Scholar
4b Negishi E. In Aspects of Mechanism and Organometallic Chemistry Plenum Press; New York: 1978. p.285

Crossref Google Scholar
5 Heck RF. In Palladium Reagents in Organic Syntheses Academic Press; New York: 1985.

Google Scholar
6a Pelter A. Smith K. Brown HC. In Borane Reagents Academic Press; San Diego, CA: 1988.

Google Scholar
6b Brown HC. Organic Syntheses via Boranes John Wiley and Sons; New York: 1975.

Google Scholar
7a Miyaura N. Yanagi T. Suzuki A. Synth. Commun. 1981, 11: 513

Google Scholar
7b Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

Google Scholar
7c Suzuki A. J. Organomet. Chem. 1999, 576: 147

Google Scholar
8a Suzuki A. Acc. Chem. Res. 1982, 15: 178

Crossref Google Scholar
8b Suzuki A. Pure Appl. Chem. 1991, 63: 419

Crossref Google Scholar
8c Benbow JW. Martinez BL. Tetrahedron Lett. 1996, 37: 8829

Crossref Google Scholar
8d Zhang H. Kwong FY. Tian Y. Chan KS. J. Org. Chem. 1998, 63: 6886

Crossref Google Scholar
9a Tsuji J. In Organic Synthesis with Palladium Compounds Springer-Verlag; Heidelberg: 1980.

Google Scholar
9b Malleron J. Fiaud J. Legros J. Handbook of Palladium-Catalyzed Organic Reactions Academic Press; San Diego, CA: 1997.

Google Scholar
10a Miyaura N. Yano T. Suzuki A. Tetrahedron Lett. 1980, 21: 2865

Google Scholar
10b Matos K. Soderquist JA. J. Org. Chem. 1998, 63: 461

Google Scholar
10c Charette AB. Gil RP. Tetrahedron Lett. 1997, 38: 2809

Google Scholar
10d Todd MH. Balasubramania S. Abell C. Tetrahedron Lett. 1997, 38: 6781

Google Scholar
10e Guille F. J. Org. Chem. 1995, 60: 292

Google Scholar
10f Johnson CN. Synlett 1998, 1025

Google Scholar
10g Wallow TI. Novak BM. J. Org. Chem. 1994, 59: 5034

Google Scholar
10h Vaultier M. Tetrahedron Lett. 1995, 36: 1443

Google Scholar
10i Guzzi U. Ielmini A. Cardamone R. Baroni M. Badone D. J. Org. Chem. 1997, 62: 7170

Google Scholar
10j Snieckus V. Wong PL. Nguyen T. Guillaneux D. Bower JF. J. Org. Chem. 1998, 63: 1514

Google Scholar
10k McCarthy JR. Strack N. Wilcoxen K. Chen C. Tetrahedron Lett. 1998, 40: 827

Google Scholar
11a Kabalka GW. Pagni RM. Tetrahedron 1997, 53: 7999

Crossref Google Scholar
11b McGinnis MB. Vagle K. Green JF. Tan L.-C. Palmer R. Pagni RM. Kabalka GW. J. Org. Chem. 1996, 61: 3496

Crossref Google Scholar
11c Sponholtz WR. Pagni RM. Kabalka GW. Green JF. Tan L.-C. J. Org. Chem. 1991, 56: 5700

Crossref Google Scholar
11d Kabalka GW. Pagni RM. Bridwell P. Walsh E. Hassaneen H. J. Org. Chem. 1981, 46: 1513

Crossref Google Scholar
11e Gaetano K. Pagni RM. Kabalka GW. Bridwell P. Walsh E. True J. Underwood M. J. Org. Chem. 1985, 50: 499

Crossref Google Scholar
11f Hondrogiannis G. Pagni RM. Kabalka GW. Anosike P. Kurt R. Tetrahedron Lett. 1990, 31: 5433

Crossref Google Scholar
11g Bains S. Pagni RM. Kabalka GW. Tetrahedron Lett. 1995, 36: 3469

Crossref Google Scholar
11h Bains S. Pagni RM. Kabalka GW. Pala C. Tetrahedron: Asymmetry 1994, 5: 821

Crossref Google Scholar
12a Kabalka GW. Pagni RM. Hair CM. Org. Lett. 1999, 1: 1423

Crossref Google Scholar
12b Kabalka GW. Pagni RM. Wang L. Namboodiri V. Hair CM. Green Chem. 2000, 2: 120

Crossref Google Scholar
13a Abramovich RA. Org. Prep. Proced. Int. 1991, 23: 683

Crossref Google Scholar
13b Whittaker AG. Mingos DMP. J. Microwave Power Electromagnetic Energy 1994, 29: 195

Crossref Google Scholar
13c Caddick S. Tetrahedron 1995, 51: 10403

Crossref Google Scholar
13d Blettner CG. Koenig WA. Wilfried A. Stenzel W. Schotten T. J. Org. Chem. 1999, 64: 3885

Crossref Google Scholar
13e Bose DS. Jayalakshmi B. J. Org. Chem. 1999, 64: 1713

Crossref Google Scholar
13f Larhed M. Hoshino M. Hadida S. Curran DP. Hallberg A. J. Org. Chem. 1997, 62: 5583

Crossref Google Scholar
13g Bendale PM. Khadilkar BM. Tetrahedron Lett. 1998, 39: 5867

Crossref Google Scholar
14a Varma RS. Pure Appl. Chem. 2001, 73: 19

Article in Thieme Connect Google Scholar
14b Varma RS. Meshram HM. Dahiya R. Synth. Commun. 2000, 30: 1249

Article in Thieme Connect Google Scholar
14c Varma RS. Green Chem. 1999, 1: 43

Article in Thieme Connect Google Scholar
14d Gutierrez E. Loupy A. Bram G. Ruiz-Hitzky E. Tetrahedron Lett. 1989, 30: 945

Article in Thieme Connect Google Scholar
14e Ben Alloum A. Labiad B. Villemin D. J. Chem. Soc., Chem. Commun. 1989, 386

Article in Thieme Connect Google Scholar
14f Ranu BC. Hajra A. Jana U. Synlett 2000, 75

Article in Thieme Connect Google Scholar
15 Smith GB. Denzeny GC. Hughes DL. King AO. Verhoever TR. J. Org. Chem. 1994, 59: 8151

Crossref Google Scholar
16a Brown HC. Bhat NG. Somayaji V. Organometallics 1992, 11: 652

Crossref Google Scholar
16b Brown HC. Scouten CG. Liotta R. J. Am. Chem. Soc. 1979, 101: 96

Crossref Google Scholar
17 Mowery ME. DeShong P. J. Org. Chem. 1999, 64: 1684

Crossref PubMed Google Scholar
18 Hendrickson JB. Wolf WA. J. Org. Chem. 1968, 33: 3610

Crossref Google Scholar
19 Dewar MJS. Hart LS. Tetrahedron 1970, 26: 1001

Crossref Google Scholar
20 Hendrickson JB. Singer M. Hussoin MS. J. Org. Chem. 1993, 58: 6913

Google Scholar
21 Klemm LH. Stevens MP. Tran LK. Sheley J. J. Heterocycl. Chem. 1988, 25: 1111

Crossref Google Scholar
22 Eisch JJ. Hallenbeck LE. Han KI. J. Am. Chem. Soc. 1968, 108: 7763

Google Scholar
23 Hermann EC. Hoyer G.-A. Kelm J. Spectrochim. Acta, Part A 1982, 38: 1057

Crossref Google Scholar
24 Brune H.-A. Hess R. Schmidtberg G. Z. Naturforsch. B.: Anorg. Chem. Org. Chem. 1984, 39: 1772

Google Scholar
25 Miles P. Suschitzky H. Tetrahedron 1963, 19: 385

Crossref Google Scholar
26 Patrick TB. Willaredt RP. DeGonia DJ. J. Org. Chem. 1985, 50: 2232

Crossref Google Scholar
27 Bei X. Turner HW. Weinberg WH. Guram AS. J. Org. Chem. 1999, 64: 6797

Crossref PubMed Google Scholar
28 Newman MS. Eberwein JA. J. Org. Chem. 1964, 29: 2516

Crossref Google Scholar
29 Cowan DO. Baum AA. J. Am. Chem. Soc. 1971, 93: 1153

Crossref Google Scholar
30 Thomas EJ. J. Chem. Soc., Perkin Trans. 1 1973, 2006

Crossref Google Scholar
31 Gomberg M. Pernert JC. J. Am. Chem. Soc. 1926, 48: 1372

Crossref Google Scholar