A Novel Silver Iodide Catalyzed Sonogashira Coupling Reaction

Pinhua Li; Lei Wang

doi:10.1055/s-2006-949640

RSS-Feed abonnieren

Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.

https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml

Teilen / Bookmarken

Facebook X Linkedin Weibo

PDF herunterladen

Synlett 2006(14): 2261-2265
DOI: 10.1055/s-2006-949640

LETTER

A Novel Silver Iodide Catalyzed Sonogashira Coupling Reaction

Pinhua Li^a, Lei Wang*^a,b
^a Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, P. R. of China
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(561)3090518; e-Mail: leiwang@hbcnc.edu.cn;

Weitere Informationen

Publikationsverlauf

Received 10 February 2006
Publikationsdatum:
24. August 2006 (online)

Abstract
Volltext
Referenzen

Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A novel and efficient Ag-catalyzed Sonogashira coupling reaction has been developed. Terminal alkynes couple with aryl iodides and aryl bromides in the presence of silver iodide, triphenylphosphine and potassium carbonate to afford the corresponding cross-coupling products in high yields.

Key words

silver iodide - Sonogashira coupling reactions - terminal alkynes - aryl iodides - aryl bromides

References and Notes

1 Stephens RD. Castro CE. J. Org. Chem. 1963, 38: 3313

Google Scholar
2 Cassar L. J. Organomet. Chem. 1975, 93: 253

Crossref Google Scholar
3 Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett. 1975, 16: 4467

Crossref Google Scholar
4a Burnagin NA. Sukhomlinova LI. Luzikova EV. Tolstaya TP. Beletskaya IP. Tetrahedron Lett. 1996, 37: 897

Google Scholar
4b Hundertmark T. Littke AF. Buchwald SL. Fu GC. Org. Lett. 2000, 2: 1729

Google Scholar
4c Erdelyi M. Gogoll A. J. Org. Chem. 2001, 66: 4165

Google Scholar
For selected reviews on the Sonogashira reaction, see:
4d Sonogashira K. In Comprehensive Organic Synthesis Vol. 3: Trost BM. Fleming I. Pergamon Press; Oxford: 1991. Chap 2.4. p.521-549

Google Scholar
4e Sonogashira K. In Metal-Catalyzed Cross-Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998. p.203-229

Google Scholar
4f Sonogashira K. In Handbook of Organopalladium Chemistry for Organic Synthesis Negishi E. Meijere A. Wiley-VCH; New York: 2002.

Google Scholar
4g Sonogashira K. J. Organomet. Chem. 2002, 653: 46

Google Scholar
4h Negishi E. Anastasia L. Chem. Rev. 2003, 103: 1979

Google Scholar
5a Paterson I. Davies RDM. Marquez R. Angew. Chem. Int. Ed. 2001, 40: 603

Crossref Google Scholar
5b Toyota M. Komori C. Ihara M. J. Org. Chem. 2000, 65: 7110

Crossref Google Scholar
5c Ioshimura F. Kawata S. Hirama M. Tetrahedron Lett. 1999, 40: 8281

Crossref Google Scholar
5d Nicolaou KC. Dai W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30: 1387

Crossref Google Scholar
6a Cosford NDP. Tehrani L. Roppe J. Schweiger E. Smith ND. Anderson J. Bristow L. Brodkin J. Jiang X. McDonald I. Rao S. Washburn M. Varney MA. J. Med. Chem. 2003, 46: 204

Crossref Google Scholar
6b Taylor EC. Dowling JE. J. Org. Chem. 1997, 62: 1599

Crossref Google Scholar
6c Nakamura H. Aizawa M. Takeuchi D. Murai A. Shimoura O. Tetrahedron Lett. 2000, 41: 2185

Crossref Google Scholar
6d Amiet G. Hügel HM. Nurlawis F. Synlett 2002, 495

Crossref Google Scholar
6e Liu T.-Z. Isobe M. Synlett 2000, 266

Crossref Google Scholar
6f Kort M. Correa V. Valentijn ARPM. Marel GA. Potter BVL. Taylor CW. Boom JH. J. Med. Chem. 2000, 43: 3295

Crossref Google Scholar
7a Nalwa HS. Miyata S. Nonlinear Optics of Organic Molecules and Polymers CRC Press; Boca Raton/FL: 1997.

Crossref Google Scholar
7b Mongin O. Porres L. Moreaux L. Merta J. Blanchard-Desce M. Org. Lett. 2002, 4: 719

Crossref Google Scholar
7c Brunsveld L. Meijer EW. Prince RB. Moore JS. J. Am. Chem. Soc. 2001, 123: 7978

Crossref Google Scholar
7d Pérez-Balderas F. Santoyo-González F. Synlett 2001, 1699

Crossref Google Scholar
7e Sonoda M. Inaba A. Itahashi K. Tobe Y. Org. Lett. 2001, 3: 2419

Crossref Google Scholar
7f Wong K.-T. Hsu CC. Org. Lett. 2001, 3: 173

Crossref Google Scholar
7g Torruellas WE. Neher D. Zanoni R. Stegeman GI. Kajzar F. Leclerc M. Chem. Phys. Lett. 1990, 175: 11

Crossref Google Scholar
7h Lee C.-H. Yamamoto T. Tetrahedron Lett. 2001, 42: 3993

Crossref Google Scholar
7i Matsumi N. Naka K. Chujo Y. J. Am. Chem. Soc. 1998, 120: 5112

Crossref Google Scholar
7j Martin RE. Diederich F. Angew. Chem. Int. Ed. 1999, 38: 1350

Crossref Google Scholar
7k Inouye M. Takahashi K. Nakazumi H. J. Am. Chem. Soc. 1999, 121: 341

Crossref Google Scholar
8a Wegner G. Müllen K. Electronic Materials: The Oligomer Approach Wiley-VCH; Weinheim: 1998.

Crossref Google Scholar
8b Li J. Ambroise A. Yang SI. Diers JR. Seth J. Wack CR. Bocian DF. Holten D. Lindsey JS. J. Am. Chem. Soc. 1999, 121: 8927

Crossref Google Scholar
8c Solomin VA. Heitz W. Macromol. Chem. Phys. 1994, 195: 303

Crossref Google Scholar
8d Strachan J.-P. Gentemann S. Seth J. Kalsbeck WA. Lindsey JS. Holten D. Bocian DF. Inorg. Chem. 1998, 37: 1191

Crossref Google Scholar
8e Wagner RW. Seth J. Yang SI. Kim D. Bocian DF. Holten D. Lindsey JS. J. Org. Chem. 1998, 63: 5042

Crossref Google Scholar
9a Höger S. Rosselli S. Ramminger A.-D. Enkelmann V. Org. Lett. 2002, 4: 4269

Crossref Google Scholar
9b Li C.-J. Slaven WT. John VT. Banerjee S. Chem. Commun. 1997, 1569

Crossref Google Scholar
10a Mongin O. Papamicael C. Hoyler N. Gossauer A. J. Org. Chem. 1998, 63: 5568

Crossref Google Scholar
10b Tobe Y. Utsumi N. Nagano A. Naemura K. Angew. Chem. Int. Ed. 1998, 37: 1285

Crossref Google Scholar
10c Onitsuka K. Fujimoto M. Ohshiro N. Takahashi S. Angew. Chem. Int. Ed. 1999, 38: 689

Crossref Google Scholar
11a Leadbeater NE. Tominack BJ. Tetrahedron Lett. 2003, 44: 8653

Google Scholar
11b Soheili A. Albaneze-Walker J. Murry JA. Dormer PG. Hughes DL. Org. Lett. 2003, 5: 4191

Google Scholar
11c Heuzé K. Méry D. Gauss D. Astruc D. Chem. Commun. 2003, 2274

Google Scholar
11d Méry D. Heuzé K. Astruc D. Chem. Commun. 2003, 1934

Google Scholar
11e Ma Y. Song C. Jiang W. Wu Q. Wang Y. Liu X. Andrus MB. Org. Lett. 2003, 5: 3317

Google Scholar
11f Djakovitch L. Rollet P. Tetrahedron Lett. 2004, 45: 1367

Google Scholar
11g Uozumi Y. Kobayashi Y. Heterocycles 2003, 59: 71

Google Scholar
11h Pal M. Parasuraman K. Gupta S. Yeleswarapu KR. Synlett 2002, 1976

Google Scholar
11i Fu X. Zhang S. Yin J. Schumacher DP. Tetrahedron Lett. 2002, 43: 6673

Google Scholar
11j Böhm VPW. Herrmann WA. Eur. J. Org. Chem. 2000, 3679

Google Scholar
11k Fu X. Zhang S. Yin J. Schumacher D. Tetrahedron Lett. 2002, 43: 6673

Google Scholar
11l Alonso DA. Nájera C. Pacheco MC. Tetrahedron Lett. 2002, 43: 9365

Google Scholar
11m Fukuyama T. Shinmen M. Nishitani S. Sato M. Ryu I. Org. Lett. 2002, 4: 1691

Google Scholar
11n Nájera C. Gil-Moltó J. Karlström S. Falvello LR. Org. Lett. 2003, 5: 1451

Google Scholar
11o Alonso DA. Nájera C. Pacheco MC. Adv. Synth. Catal. 2003, 345: 1146

Google Scholar
11p Buchmeiser MR. Schareina T. Kempe R. Wurst K. J. Organomet. Chem. 2001, 634: 39

Google Scholar
11q Bertus P. Pale P. J. Organomet. Chem. 1998, 567: 173

Google Scholar
11r Bertus P. Pale P. Tetrahedron Lett. 1996, 37: 2019

Google Scholar
11s Bertus P. Pale P. Tetrahedron Lett. 1997, 38: 8193

Google Scholar
11t Halbes U. Pale P. J. Organomet. Chem. 2003, 687: 420

Google Scholar
11u
It should be noted that the copper-free Sonogashira coupling reactions are representative and not comprehensive in this paper.
12a Cheng J. Sun Y. Wang F. Guo M. Xu J.-H. Pan Y. Zhang Z. J. Org. Chem. 2004, 69: 5428

Crossref Google Scholar
12b Arques A. Aunon D. Molina P. Tetrahedron Lett. 2004, 45: 4337

Crossref Google Scholar
12c Mori A. Kawashima J. Shimada T. Suguro M. Hirabayashi K. Nishihara Y. Org. Lett. 2000, 2: 2935

Crossref Google Scholar
12d Alonso DA. Najera C. Pacheco MC. Tetrahedron Lett. 2002, 43: 9365

Crossref Google Scholar
12e Gelman D. Buchwald SL. Angew. Chem. Int. Ed. 2003, 42: 5993

Crossref Google Scholar
12f Halbes U. Bertus P. Pale P. Tetrahedron Lett. 2001, 42: 8641

Crossref Google Scholar
12g Halbes U. Bertus P. Pale P. Eur. J. Org. Chem. 2001, 4391

Crossref Google Scholar
12h Halbes U. Pale P. Tetrahedron Lett. 2002, 43: 2039

Crossref Google Scholar
12i Halbes U. Vasiliev A. Pale P. Eur. J. Org. Chem. 2005, 2828

Crossref Google Scholar
13 Choudary BM. Madhi S. Chowdari NS. Kantam ML. Sreedhar B. J. Am. Chem. Soc. 2002, 124: 14127

Crossref PubMed Google Scholar
14 Urgaonkar S. Verkade JG. J. Org. Chem. 2004, 69: 5752

Crossref PubMed Google Scholar
15a Beletskaya IP. Latyshev GV. Tsvetkov AV. Lukashev NV. Tetrahedron Lett. 2003, 44: 5011

Crossref Google Scholar
15b Wang L. Li P. Zhang Y. Chem. Commun. 2004, 514

Crossref Google Scholar
16 Ma D. Liu F. Chem. Commun. 2004, 1934

Crossref Google Scholar
17 Leadbeater NE. Marco M. Tominack BJ. Org. Lett. 2003, 5: 3919

Crossref PubMed Google Scholar
18a Cui Y. He C. Angew. Chem. Int. Ed. 2004, 43: 4210

Google Scholar
18b Wei C. Li Z. Li CJ. Org. Lett. 2003, 5: 4473

Google Scholar
18c Yao X. Li CJ. Org. Lett. 2005, 7: 4395

Google Scholar
19a Mori A. Kawashima J. Shimada T. Suguro M. Hirabayashi K. Nishihara Y. Org. Lett. 2000, 2: 2935

Crossref Google Scholar
19b Zou G. Zhu J. Tang J. Tetrahedron Lett. 2003, 44: 8709

Crossref Google Scholar
21a Leadbeater NE. Marco M. Angew. Chem. Int. Ed. 2003, 42: 1407

Crossref Google Scholar
21b Leadbeater NE. Marco M. J. Org. Chem. 2003, 68: 5660

Crossref Google Scholar
22a Arvela RK. Leadbeater NE. Sangi MS. Williams VA. Granados P. Singer RD. J. Org. Chem. 2005, 70: 161

Crossref Google Scholar
22b Halbes-Letinois U. Pale P. Berger S. Magn. Reson. Chem. 2004, 42: 831

Crossref Google Scholar
23a Létinois-Halbes U. Pale P. Berger S. J. Org. Chem. 2005, 70: 9185

Crossref Google Scholar
23b Létinois-Halbes U. Pale P. Berger S. Magn. Reson. Chem. 2004, 42: 831

Crossref Google Scholar
24 Arcadi A. Cacchi S. Fabrizi G. Marinelli F. Pace P. Eur. J. Org. Chem. 1999, 12: 3305

Google Scholar
25 Yoshida K. Fueno T. J. Org. Chem. 1973, 38: 1045

Crossref Google Scholar

20

The unique Sonogashira coupling products were characterized by mp, ¹H NMR and ¹³C NMR, and MS.
(4-Acetylphenyl)phenylacetylene: mp 95-96 °C (Lit.²⁴ 94-96 °C). ¹H NMR (250 MHz, CDCl₃): δ = 7.91 (d, J = 8.41 Hz, 2 H), 7.58 (d, J = 8.41 Hz, 2 H), 7.52-7.54 (m, 2 H), 7.33-7.36 (m, 3 H), 2.57 (s, 3 H). ¹³C NMR (62.5 MHz, CDCl₃): δ = 197.1, 136.1, 131.7, 131.6, 128.7, 128.4, 128.2, 128.1, 122.6, 92.6, 88.6, 26.5. MS (relative intensity, %): m/z = 220 (60) [M⁺], 205 (100), 176 (48), 151 (18), 102 (10), 88 (19).
(4-Cyanophenyl)phenylacetylene: mp 109-110 °C (Lit.²⁵ 108.5-109.5 °C). ¹H NMR (300 MHz, CDCl₃): δ = 7.59-7.66 (m, 4 H), 7.53-7.57 (m, 2 H), 7.36-7.40 (m, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 132.0 (2 × C), 131.8, 129.1, 128.5, 128.2, 122.2, 118.5, 111.4, 93.7, 87.7. MS: (relative intensity, %): m/z = 203 (100) [M⁺], 176 (8), 151 (5), 75 (5).
(3-Cyanophenyl)phenylacetylene: mp 69-71 °C (Lit.²⁵ 70-71 °C). ¹H NMR (300 MHz, CDCl₃): δ = 7.79 (t, J = 1.50 Hz, 1 H), 7.73 (dt, J = 1.50, 7.80 Hz, 1 H), 7.59 (dt, J = 1.50, 7.80 Hz, 1 H), 7.52-7.55 (m, 2 H), 7.45 (t, J = 7.80 Hz, 1 H), 7.35-7.39 (m, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 135.6, 134.8, 131.7, 131.3, 129.2, 128.9, 128.4, 124.8, 122.2, 118.0, 112.8, 91.7, 86.8. MS (relative intensity, %): m/z = 203 (100) [M⁺], 176 (7), 151 (5), 75 (5).