Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2010(12): 1845-1848
DOI: 10.1055/s-0030-1258116
DOI: 10.1055/s-0030-1258116
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New YorkTransition-Metal-Catalyzed Cross-Couplings of Aryl Tosylates or Mesylates with Organoindium Reagents
Further Information
Received
16 March 2010
Publication Date:
30 June 2010 (online)
Publication History
Publication Date:
30 June 2010 (online)

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 for this article is available online:
- Supporting Information
- For selected examples, see:
- 1a
Pena MA.Sestelo JP.Sarandeses LA. J. Org. Chem. 2007, 72: 1271MissingFormLabel - 1b
Xue Z.Yang D.Wang C. J. Organomet. Chem. 2006, 691: 247MissingFormLabel - 1c
Riveiros R.Rodriguez D.Sestelo JP.Sarandeses LA. Org. Lett. 2006, 8: 1403MissingFormLabel - 1d
Kim S.Seomoon D.Lee PH. Chem. Commun. 2009, 1873MissingFormLabel - 1e
Pena MA.Sestelo JP.Sarandeses LA. Synthesis 2005, 485MissingFormLabel - 1f
Takami K.Mikami S.Yorimitsu H.Shinokubo H.Oshima K. J. Org. Chem. 2003, 68: 6627MissingFormLabel - 1g
Lee PH.Lee SW.Lee K. Org. Lett. 2003, 5: 1103MissingFormLabel - 1h
Perez I.Sestelo JP.Sarandeses LA. J. Am. Chem. Soc. 2001, 123: 4155MissingFormLabel - 1i
Lee PH.Lee K.Kang Y.
J. Am. Chem. Soc. 2006, 128: 1139MissingFormLabel - 1j
Seomoon D.Lee K.Kim H.Lee PH. Chem. Eur. J. 2007, 13: 5197MissingFormLabel - 1k
Lee PH.Lee J. J. Org. Chem. 2008, 73: 7413MissingFormLabel - 1l
Zhao Y.Jin L.Li P.Lei A. J. Am. Chem. Soc. 2008, 130: 9429MissingFormLabel - 1m
Chen Y.-H.Knochel P. Angew. Chem. Int. Ed. 2008, 47: 7648MissingFormLabel - 2a
So CM.Lau CP.Chan ASC.Kwong FY. J. Am. Chem. Soc. 2008, 73: 7731MissingFormLabel - 2b
So CM.Lau CP.Chan ASC.Kwong FY. J. Org. Chem. 2008, 73: 7731MissingFormLabel - 2c
So CM.Lee HW.Lau CP.Kwong FY. Org. Lett. 2009, 11: 317MissingFormLabel - 2d
Kuroda J.Inamota K.Hiroya K.Doi T. Eur. J. Org. Chem. 2009, 2251MissingFormLabel - 2e
So CM.Lau CP.Kwong FY. Angew. Chem. Int. Ed. 2008, 47: 8059MissingFormLabel - 2f
Ogata T.Hartwig JF. J. Am. Chem. Soc. 2008, 130: 13848MissingFormLabel - 2g
Fors BP.Watson DA.Biscoe MR.Buchwald SL. J. Am. Chem. Soc. 2008, 130: 13552MissingFormLabel - 2h
So CM.Zhou Z.Lau CP.Kwong FY. Angew. Chem. Int. Ed. 2008, 47: 6402MissingFormLabel - 2i
Munday RH.Martinelli JR.Buchwald SL. J. Am. Chem. Soc. 2008, 130: 2754MissingFormLabel - 3a
Nguyen HN.Huang X.Buchwald SL. J. Am. Chem. Soc. 2003, 125: 11818MissingFormLabel - 3b
Tang Z.-Y.Hu Q.-S. J. Am. Chem. Soc. 2004, 126: 3058MissingFormLabel - 3c
Zim D.Lando VR.Dupont J.Monteiro AL. Org. Lett. 2001, 3: 3049MissingFormLabel - 3d
Lakshman MK.Thomson PF.Nuqui MA.Hilmer JH.Sevova N.Boggess B. Org. Lett. 2002, 4: 1479MissingFormLabel - 3e
Huffman MA.Yasuda N. Synlett 1999, 471MissingFormLabel - 3f
Wu J.Zhang L.Luo Y. Tetrahedron Lett. 2006, 47: 6747MissingFormLabel - 3g
Wu J.Zhang L.Xia H.-G. Tetrahedron Lett. 2006, 47: 1525MissingFormLabel - 3h
Wu J.Zhang L.Gao K. Eur. J. Org. Chem. 2006, 5260MissingFormLabel - 3i
Baxter JM.Steinhuebel D.Palucki M.Davies IW. Org. Lett. 2005, 7: 215MissingFormLabel - 3j
Zhang L.Meng T.Wu J. J. Org. Chem. 2007, 72: 9346MissingFormLabel - 3k
Steinhuebel D.Baxter JM.Palucki M.Davies IW. J. Org. Chem. 2005, 70: 10124MissingFormLabel - 3l
Netherton MR.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 3910MissingFormLabel - 3m
Zhang L.Meng T.Fan R.Wu J. J. Org. Chem. 2007, 72: 7279MissingFormLabel - 3n
Wu J.Zhu Q.Wang L.Fathi R.Yang Z. J. Org. Chem. 2003, 68: 670MissingFormLabel - 3o
Wu J.Wang L.Fathi R.Yang Z. Tetrahedron Lett. 2002, 43: 4395MissingFormLabel - 3p
Tang Z.-Y.Hu Q.-S. Adv. Synth. Catal. 2004, 346: 1635MissingFormLabel - 3q
Gao W.Luo Y.Ding Q.Peng Y.Wu J. Tetrahedron Lett. 2010, 51: 136MissingFormLabel - 4a
Fu X.Zhang S.Yin J.Schumacher DP. Tetrahedron Lett. 2002, 43: 6673MissingFormLabel - 4b
Wu J.Liao Y.Yang Z. J. Org. Chem. 2001, 66: 3642MissingFormLabel - 4c
Ackermann L.Gschrei CJ.Althammer A.Riederer M. Chem. Commun. 2006, 1419MissingFormLabel - 4d
Wolf C.Lerebours R. Org. Lett. 2004, 6: 1147MissingFormLabel - 4e
Gelman D.Buchwald SL. Angew. Chem. Int. Ed. 2003, 42: 5993MissingFormLabel - Heck coupling:
- 4f
Fu X.Zhang S.Yin J.McAllister TL.Jiang SA.Tann C.-H.Thiruvengadam TK.Zhang F. Tetrahedron Lett. 2002, 43: 573MissingFormLabel - 4g
Hansen AL.Skrydstrup T. Org. Lett. 2005, 7: 5585MissingFormLabel - 4h
Hansen AL.Ebran J.-P.Ahlquist M.Norrby P.-O.Skrydstrup T. Angew. Chem. Int. Ed. 2006, 45: 3349MissingFormLabel - 5a
Roy AH.Hartwig JF. J. Am. Chem. Soc. 2003, 125: 8704MissingFormLabel - 5b
Limmert ME.Roy AH.Hartwig JF. J. Org. Chem. 2005, 70: 9364MissingFormLabel - 5c
Ackermann L.Althammer A. Org. Lett. 2006, 8: 3457MissingFormLabel - 5d
Fürstner A.Leitner A.Mendez M.Krause H. J. Am. Chem. Soc. 2002, 124: 13856MissingFormLabel - 5e
Badone D.Cecchi R.Guzzi U. J. Org. Chem. 1992, 57: 6321MissingFormLabel - 5f
Nagatsugi F.Uemura K.Nakashima S.Minoru M.Sasaki S. Tetrahedron Lett. 1995, 36: 421MissingFormLabel - 5g
Schio L.Chatreaux F.Klich M. Tetrahedron Lett. 2000, 41: 1543MissingFormLabel - 5h
Zhou J.Fu GC. J. Am. Chem. Soc. 2003, 125: 12527MissingFormLabel - 5i
Wu J.Sun X.Zhang L. Chem. Lett. 2005, 34: 796MissingFormLabel - 5j
Zhang L.Wu J. J. Am. Chem. Soc. 2008, 130: 12250MissingFormLabel - 5k
Zhang L.Qing J.Yang P.Wu J. Org. Lett. 2008, 10: 4971MissingFormLabel - 6a
Hamann BC.Hartwig JF. J. Am. Chem. Soc. 1998, 120: 7369MissingFormLabel - 6b
Fernández-Rodríguez MA.Shen Q.Hartwig JF. J. Am. Chem. Soc. 2006, 128: 2180MissingFormLabel - 6c
Klapars A.Campos KR.Chen C.Volante RP. Org. Lett. 2005, 7: 1185MissingFormLabel - Nickel-catalyzed C-C bond couplings of aryl mesylates, see:
- 7a
Kobayashi Y.Mizojiri R. Tetrahedron Lett. 1996, 37: 8531MissingFormLabel - 7b
Ueda M.Saitoh A.Oh-tani S.Miyaura N. Tetrahedron 1998, 54: 13079MissingFormLabel - 7c
Percec V.Bae J.-Y.Zhao M.Hill DH. J. Org. Chem. 1995, 60: 176MissingFormLabel - 7d
Percec V.Bae J.-Y.Hill DH. J. Org. Chem. 1995, 60: 1060MissingFormLabel - 7e
Percec V.Bae J.-Y.Hill DH. J. Org. Chem. 1995, 60: 1066MissingFormLabel - 7f
Percec V.Bae J.-Y.Hill DH. J. Org. Chem. 1995, 60: 6895MissingFormLabel - 7g
Ueda M.Saitoh A.Oh-tani S.Miyuara N. J. Org. Chem. 1997, 62: 8024MissingFormLabel - 7h
Percec V.Golding GM.Smidrkal J.Weichold O. J. Org. Chem. 2004, 69: 3447MissingFormLabel - 7i
Tang Z.-Y.Spinella S.Hu Q.-S. Tetrahedron Lett. 2006, 47: 2427MissingFormLabel - 7j
Lipshutz BH.Butler T.Swift E. Org. Lett. 2008, 10: 697MissingFormLabel - 7k
Gao C.-Y.Yang L.-M. J. Org. Chem. 2008, 73: 1624MissingFormLabel - 7l
Lei J.-G.Xu M.-H.Lin G.-Q. Synlett 2004, 2364MissingFormLabel - 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 - 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 - 10
Wang Z.Fan R.Wu J. Adv. Synth. Catal. 2007, 349: 1943 - 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: 14468MissingFormLabel - 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: 3268MissingFormLabel - 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: 14656MissingFormLabel - 11d
Fürstner A.Leitner A. Angew. Chem. Int. Ed. 2002, 41: 609MissingFormLabel - 11e
Quasdorf KW.Tian X.Garg NK. J. Am. Chem. Soc. 2008, 130: 14422MissingFormLabel - 11f
Li B.-J.Li Y.-Z.Lu X.-Y.Liu J.Guan B.-T.Shi Z.-J. Angew. Chem. Int. Ed. 2008, 47: 10124MissingFormLabel - 11g
Goossen LJ.Goossen K.Stanciu C. Angew. Chem. Int. Ed. 2009, 48: 3569MissingFormLabel - 11h
Li Z.Zhang S.-L.Fu Y.Guo Q.-X.Liu L.
J. Am. Chem. Soc. 2009, 131: 8815MissingFormLabel - 11i
Guan B.-T.Xiang S.-K.Wu T.Sun Z.-P.Wang B.-Q.Zhao K.-Q.Shi Z.-J. Chem. Commun. 2008, 1437MissingFormLabel - 11j
Tobisu M.Shimasaki T.Chatani N. Angew. Chem. Int. Ed. 2008, 47: 4866MissingFormLabel