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

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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

Further Information

Publication History

Received 16 March 2010
Publication Date:
30 June 2010 (online)

Abstract
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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

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

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

Google Scholar
1d Kim S. Seomoon D. Lee PH. Chem. Commun. 2009, 1873

Google Scholar
1e Pena MA. Sestelo JP. Sarandeses LA. Synthesis 2005, 485

Google Scholar
1f Takami K. Mikami S. Yorimitsu H. Shinokubo H. Oshima K. J. Org. Chem. 2003, 68: 6627

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

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

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

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

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

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

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

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

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

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

Google Scholar
2d Kuroda J. Inamota K. Hiroya K. Doi T. Eur. J. Org. Chem. 2009, 2251

Google Scholar
2e So CM. Lau CP. Kwong FY. Angew. Chem. Int. Ed. 2008, 47: 8059

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

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

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

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

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

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

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

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

Google Scholar
3e Huffman MA. Yasuda N. Synlett 1999, 471

Google Scholar
3f Wu J. Zhang L. Luo Y. Tetrahedron Lett. 2006, 47: 6747

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

Google Scholar
3h Wu J. Zhang L. Gao K. Eur. J. Org. Chem. 2006, 5260

Google Scholar
3i Baxter JM. Steinhuebel D. Palucki M. Davies IW. Org. Lett. 2005, 7: 215

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

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

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

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

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

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

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

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

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

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

Google Scholar
4c Ackermann L. Gschrei CJ. Althammer A. Riederer M. Chem. Commun. 2006, 1419

Google Scholar
4d Wolf C. Lerebours R. Org. Lett. 2004, 6: 1147

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Google Scholar
7l Lei J.-G. Xu M.-H. Lin G.-Q. Synlett 2004, 2364

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

Crossref 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

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

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

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

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

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

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

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

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

Google Scholar
11j Tobisu M. Shimasaki T. Chatani N. Angew. Chem. Int. Ed. 2008, 47: 4866

Google Scholar

Supplementary Material

Supporting Information