Transition-Metal-Catalyzed
Cross-Couplings of Aryl Tosylates or Mesylates with Organoindium
Reagents

Liang Zhang; Yong Luo; Jie Wu

doi:10.1055/s-0030-1258116

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 2010(12): 1845-1848
DOI: 10.1055/s-0030-1258116

LETTER

Transition-Metal-Catalyzed Cross-Couplings of Aryl Tosylates or Mesylates with Organoindium Reagents

Liang Zhang^a, Yong Luo^a, Jie Wu*^,a,b
^a Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China
Fax: +86(21)65641740; e-Mail: jie_wu@fudan.edu.cn;
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China

Weitere Informationen

Publikationsverlauf

Received 16 March 2010
Publikationsdatum:
30. Juni 2010 (online)

Abstract
Volltext
Referenzen
Zusatzmaterial

Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

The first example of transition-metal-catalyzed cross-coupling reactions of aryl tosylates or mesylates with organoindium compounds is described. The desired carbon-carbon bond formation proceeds under mild conditions to generate the coupling products in good yields.

Key words

aryl tosylate - aryl mesylate - cross-coupling reaction - organoindium compound - transition metal

Supporting Information

References

For selected examples, see:
1a Pena MA. Sestelo JP. Sarandeses LA. J. Org. Chem. 2007, 72: 1271

Suche in Google Scholar
1b Xue Z. Yang D. Wang C. J. Organomet. Chem. 2006, 691: 247

Suche in Google Scholar
1c Riveiros R. Rodriguez D. Sestelo JP. Sarandeses LA. Org. Lett. 2006, 8: 1403

Suche in Google Scholar
1d Kim S. Seomoon D. Lee PH. Chem. Commun. 2009, 1873
1e Pena MA. Sestelo JP. Sarandeses LA. Synthesis 2005, 485
1f Takami K. Mikami S. Yorimitsu H. Shinokubo H. Oshima K. J. Org. Chem. 2003, 68: 6627

Suche in Google Scholar
1g Lee PH. Lee SW. Lee K. Org. Lett. 2003, 5: 1103

Suche in Google Scholar
1h Perez I. Sestelo JP. Sarandeses LA. J. Am. Chem. Soc. 2001, 123: 4155

Suche in Google Scholar
1i Lee PH. Lee K. Kang Y.
J. Am. Chem. Soc. 2006, 128: 1139

Suche in Google Scholar
1j Seomoon D. Lee K. Kim H. Lee PH. Chem. Eur. J. 2007, 13: 5197

Suche in Google Scholar
1k Lee PH. Lee J. J. Org. Chem. 2008, 73: 7413

Suche in Google Scholar
1l Zhao Y. Jin L. Li P. Lei A. J. Am. Chem. Soc. 2008, 130: 9429

Suche in Google Scholar
1m Chen Y.-H. Knochel P. Angew. Chem. Int. Ed. 2008, 47: 7648

Suche in Google Scholar
2a So CM. Lau CP. Chan ASC. Kwong FY. J. Am. Chem. Soc. 2008, 73: 7731

Suche in Google Scholar
2b So CM. Lau CP. Chan ASC. Kwong FY. J. Org. Chem. 2008, 73: 7731

Suche in Google Scholar
2c So CM. Lee HW. Lau CP. Kwong FY. Org. Lett. 2009, 11: 317

Suche in Google Scholar
2d Kuroda J. Inamota K. Hiroya K. Doi T. Eur. J. Org. Chem. 2009, 2251
2e So CM. Lau CP. Kwong FY. Angew. Chem. Int. Ed. 2008, 47: 8059

Suche in Google Scholar
2f Ogata T. Hartwig JF. J. Am. Chem. Soc. 2008, 130: 13848

Suche in Google Scholar
2g Fors BP. Watson DA. Biscoe MR. Buchwald SL. J. Am. Chem. Soc. 2008, 130: 13552

Suche in Google Scholar
2h So CM. Zhou Z. Lau CP. Kwong FY. Angew. Chem. Int. Ed. 2008, 47: 6402

Suche in Google Scholar
2i Munday RH. Martinelli JR. Buchwald SL. J. Am. Chem. Soc. 2008, 130: 2754

Suche in Google Scholar
3a Nguyen HN. Huang X. Buchwald SL. J. Am. Chem. Soc. 2003, 125: 11818

Suche in Google Scholar
3b Tang Z.-Y. Hu Q.-S. J. Am. Chem. Soc. 2004, 126: 3058

Suche in Google Scholar
3c Zim D. Lando VR. Dupont J. Monteiro AL. Org. Lett. 2001, 3: 3049

Suche in Google Scholar
3d Lakshman MK. Thomson PF. Nuqui MA. Hilmer JH. Sevova N. Boggess B. Org. Lett. 2002, 4: 1479

Suche in Google Scholar
3e Huffman MA. Yasuda N. Synlett 1999, 471
3f Wu J. Zhang L. Luo Y. Tetrahedron Lett. 2006, 47: 6747

Suche in Google Scholar
3g Wu J. Zhang L. Xia H.-G. Tetrahedron Lett. 2006, 47: 1525

Suche in Google Scholar
3h Wu J. Zhang L. Gao K. Eur. J. Org. Chem. 2006, 5260
3i Baxter JM. Steinhuebel D. Palucki M. Davies IW. Org. Lett. 2005, 7: 215

Suche in Google Scholar
3j Zhang L. Meng T. Wu J. J. Org. Chem. 2007, 72: 9346

Suche in Google Scholar
3k Steinhuebel D. Baxter JM. Palucki M. Davies IW. J. Org. Chem. 2005, 70: 10124

Suche in Google Scholar
3l Netherton MR. Fu GC. Angew. Chem. Int. Ed. 2002, 41: 3910

Suche in Google Scholar
3m Zhang L. Meng T. Fan R. Wu J. J. Org. Chem. 2007, 72: 7279

Suche in Google Scholar
3n Wu J. Zhu Q. Wang L. Fathi R. Yang Z. J. Org. Chem. 2003, 68: 670

Suche in Google Scholar
3o Wu J. Wang L. Fathi R. Yang Z. Tetrahedron Lett. 2002, 43: 4395

Suche in Google Scholar
3p Tang Z.-Y. Hu Q.-S. Adv. Synth. Catal. 2004, 346: 1635

Suche in Google Scholar
3q Gao W. Luo Y. Ding Q. Peng Y. Wu J. Tetrahedron Lett. 2010, 51: 136

Suche in Google Scholar
4a Fu X. Zhang S. Yin J. Schumacher DP. Tetrahedron Lett. 2002, 43: 6673

Suche in Google Scholar
4b Wu J. Liao Y. Yang Z. J. Org. Chem. 2001, 66: 3642

Suche in Google Scholar
4c Ackermann L. Gschrei CJ. Althammer A. Riederer M. Chem. Commun. 2006, 1419
4d Wolf C. Lerebours R. Org. Lett. 2004, 6: 1147

Suche in Google Scholar
4e Gelman D. Buchwald SL. Angew. Chem. Int. Ed. 2003, 42: 5993

Suche in Google Scholar
Heck coupling:
4f Fu X. Zhang S. Yin J. McAllister TL. Jiang SA. Tann C.-H. Thiruvengadam TK. Zhang F. Tetrahedron Lett. 2002, 43: 573

Suche in Google Scholar
4g Hansen AL. Skrydstrup T. Org. Lett. 2005, 7: 5585

Suche in Google Scholar
4h Hansen AL. Ebran J.-P. Ahlquist M. Norrby P.-O. Skrydstrup T. Angew. Chem. Int. Ed. 2006, 45: 3349

Suche in Google Scholar
5a Roy AH. Hartwig JF. J. Am. Chem. Soc. 2003, 125: 8704

Suche in Google Scholar
5b Limmert ME. Roy AH. Hartwig JF. J. Org. Chem. 2005, 70: 9364

Suche in Google Scholar
5c Ackermann L. Althammer A. Org. Lett. 2006, 8: 3457

Suche in Google Scholar
5d Fürstner A. Leitner A. Mendez M. Krause H. J. Am. Chem. Soc. 2002, 124: 13856

Suche in Google Scholar
5e Badone D. Cecchi R. Guzzi U. J. Org. Chem. 1992, 57: 6321

Suche in Google Scholar
5f Nagatsugi F. Uemura K. Nakashima S. Minoru M. Sasaki S. Tetrahedron Lett. 1995, 36: 421

Suche in Google Scholar
5g Schio L. Chatreaux F. Klich M. Tetrahedron Lett. 2000, 41: 1543

Suche in Google Scholar
5h Zhou J. Fu GC. J. Am. Chem. Soc. 2003, 125: 12527

Suche in Google Scholar
5i Wu J. Sun X. Zhang L. Chem. Lett. 2005, 34: 796

Suche in Google Scholar
5j Zhang L. Wu J. J. Am. Chem. Soc. 2008, 130: 12250

Suche in Google Scholar
5k Zhang L. Qing J. Yang P. Wu J. Org. Lett. 2008, 10: 4971

Suche in Google Scholar
6a Hamann BC. Hartwig JF. J. Am. Chem. Soc. 1998, 120: 7369

Suche in Google Scholar
6b Fernández-Rodríguez MA. Shen Q. Hartwig JF. J. Am. Chem. Soc. 2006, 128: 2180

Suche in Google Scholar
6c Klapars A. Campos KR. Chen C. Volante RP. Org. Lett. 2005, 7: 1185

Suche in Google Scholar
Nickel-catalyzed C-C bond couplings of aryl mesylates, see:
7a Kobayashi Y. Mizojiri R. Tetrahedron Lett. 1996, 37: 8531

Suche in Google Scholar
7b Ueda M. Saitoh A. Oh-tani S. Miyaura N. Tetrahedron 1998, 54: 13079

Suche in Google Scholar
7c Percec V. Bae J.-Y. Zhao M. Hill DH. J. Org. Chem. 1995, 60: 176

Suche in Google Scholar
7d Percec V. Bae J.-Y. Hill DH. J. Org. Chem. 1995, 60: 1060

Suche in Google Scholar
7e Percec V. Bae J.-Y. Hill DH. J. Org. Chem. 1995, 60: 1066

Suche in Google Scholar
7f Percec V. Bae J.-Y. Hill DH. J. Org. Chem. 1995, 60: 6895

Suche in Google Scholar
7g Ueda M. Saitoh A. Oh-tani S. Miyuara N. J. Org. Chem. 1997, 62: 8024

Suche in Google Scholar
7h Percec V. Golding GM. Smidrkal J. Weichold O. J. Org. Chem. 2004, 69: 3447

Suche in Google Scholar
7i Tang Z.-Y. Spinella S. Hu Q.-S. Tetrahedron Lett. 2006, 47: 2427

Suche in Google Scholar
7j Lipshutz BH. Butler T. Swift E. Org. Lett. 2008, 10: 697

Suche in Google Scholar
7k Gao C.-Y. Yang L.-M. J. Org. Chem. 2008, 73: 1624

Suche in Google Scholar
7l Lei J.-G. Xu M.-H. Lin G.-Q. Synlett 2004, 2364
8 Albaneze-Walker J. Raju J. Vance JA. Goodman AJ. Reeder MR. Liao J. Maust MT. Irish PA. Espino P. Andrews DR. Org. Lett. 2009, 11: 1463

Crossref Suche in Google Scholar
9 For mechanistic studies on Pd-mediated oxidative addition of aryl tosylates, see: Roy AH. Hartwig JF. Organometallics 2004, 23: 194 ; and references cited therein

Crossref Suche in Google Scholar
10 Wang Z. Fan R. Wu J. Adv. Synth. Catal. 2007, 349: 1943

Crossref Suche in Google Scholar
For recent selected examples, see:
11a Guan B.-T. Wang Y. Li B.-J. Yu D.-G. Shi Z.-J. J. Am. Chem. Soc. 2008, 130: 14468

Suche in Google Scholar
11b Guan B.-T. Xiang S.-K. Wang B.-Q. Sun Z.-P. Wang Y. Zhao K.-Q. Shi Z.-J. J. Am. Chem. Soc. 2008, 130: 3268

Suche in Google Scholar
11c Li B.-J. Xu L. Wu Z.-H. Guan B.-T. Sun C.-L. Wang B.-Q. Shi Z.-J. J. Am. Chem. Soc. 2009, 131: 14656

Suche in Google Scholar
11d Fürstner A. Leitner A. Angew. Chem. Int. Ed. 2002, 41: 609

Suche in Google Scholar
11e Quasdorf KW. Tian X. Garg NK. J. Am. Chem. Soc. 2008, 130: 14422

Suche in Google Scholar
11f Li B.-J. Li Y.-Z. Lu X.-Y. Liu J. Guan B.-T. Shi Z.-J. Angew. Chem. Int. Ed. 2008, 47: 10124

Suche in Google Scholar
11g Goossen LJ. Goossen K. Stanciu C. Angew. Chem. Int. Ed. 2009, 48: 3569

Suche in Google Scholar
11h Li Z. Zhang S.-L. Fu Y. Guo Q.-X. Liu L.
J. Am. Chem. Soc. 2009, 131: 8815

Suche in Google Scholar
11i Guan B.-T. Xiang S.-K. Wu T. Sun Z.-P. Wang B.-Q. Zhao K.-Q. Shi Z.-J. Chem. Commun. 2008, 1437
11j Tobisu M. Shimasaki T. Chatani N. Angew. Chem. Int. Ed. 2008, 47: 4866

Suche in Google Scholar

Zusatzmaterial

Supporting Information