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
Synlett 2008(7): 949-957
DOI: 10.1055/s-2008-1042907
DOI: 10.1055/s-2008-1042907
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York
Recent Advances in Direct Arylation via Palladium-Catalyzed Aromatic C-H Activation
Weitere Informationen
Received
22 October 2007
Publikationsdatum:
11. März 2008 (online)
Publikationsverlauf
Publikationsdatum:
11. März 2008 (online)
Abstract
Highly selective arylation catalyzed by palladium and directed by the acetamino group provides an efficient and practical protocol for constructing unique biaryl scaffolds, which could be further transformed into different structural units found in a range of natural products.
1 Introduction
2 Highly Regioselective Halogenation
3 Highly Regioselective Arylation
3.1 With Arylboronic Acids
3.2 With Trialkoxyarylsilanes
3.3 With Simple Arenes
3.4 Further Transformations
4 Conclusion
Key words
C-H activation - arylation - palladium - catalysis - acetanilide
- 1
Dyker G. Handbook of C-H Transformations. Applications in Organic Synthesis Wiley-VCH; Weinheim: 2005. -
2a
Labinger JA.Bercaw JE. Nature (London) 2002, 417: 507 -
2b
Jones W.Feher F. Acc. Chem. Res. 1989, 22: 91 -
3a
Shilov AE.Shul’pin GB. Chem. Rev. 1997, 97: 2879 -
3b
Shi Z.He C. J. Am. Chem. Soc. 2004, 126: 13596 -
3c
Shi Z.He C. J. Org. Chem. 2004, 69: 3669 -
3d
Hennessy E.Buchwald SL. J. Am. Chem. Soc. 2003, 125: 12084 -
3e
Hashmi ASK.Schwarz L.Choi JH.Frost TM. Angew. Chem. Int. Ed. 2000, 39: 2285 -
3f
Wang X.Lane BS.Sames D. J. Am. Chem. Soc. 2005, 127: 4996 -
3g
Alexakis A.Tomassini A.Andrey O.Bernardinelli G. Eur. J. Org. Chem. 2005, 1332 -
4a
Hartwig JF. In Handbook of Organopalladium Chemistry for Organic SynthesisNegishi E.-i.de Meijere A. Wiley-Interscience; New York: 2002. p.1051 -
4b
Yang BH.Buchwald SL. J. Organomet. Chem. 1999, 576: 125 -
5a
Metal-Catalyzed Cross-Coupling Reactions
Diederich F.Stang PJ. Wiley-VCH; New York: 1998. -
5b
de Meijere A.Diederich F. Metal-Catalyzed Cross-Coupling Reactions Wiley-VCH; Weinheim: 2004. -
6a
Murai S. Activation of Unreactive Bonds and Organic Synthesis Springer-Verlag; Berlin: 1999. p.48-78 -
6b
Kakiuchi F.Chatani N. Adv. Synth. Catal. 2003, 345: 1077 -
6c
Dyker G. Angew. Chem. Int. Ed. 1999, 38: 1699 -
6d
Stahl SS.Labinger JA.Bercaw JE. Angew. Chem. Int. Ed. 1998, 37: 2180 - 7 For an example, see:
Dimroth O. Ber. Dtsch. Chem. Ges. 1898, 31: 2154 -
8a
Shul’pin GB.Shilov AE.Kitaigorodskii AN.Zeile-Krevor JV. J. Organomet. Chem. 1980, 201: 319 -
8b
Shul’pin GB.Nizova GV.Shilov AE. J. Chem. Soc., Chem. Commun. 1983, 671 -
8c
Serdobov MV.Nizova GV.Shul’pin GB. J. Organomet. Chem. 1984, 265: 12 -
8d
Aoyama Y.Yoshida T.Sakurai K.Ogoshi H. Organometallics 1986, 5: 168 -
8e
Ueda T.Yamanaka H.Adachi T.Yoshida T. Chem. Lett. 1988, 525 -
8f
Johnson TJ.Alvey LJ.Brady M.Mayne CL.Arif AM.Gladysz JA. Chem. Eur. J. 1995, 1: 294 -
8g
Solari E.Musso F.Ferguson R.Floriani C.Chiesi-Villa A.Rizzoli C. Angew. Chem., Int. Ed. Engl. 1995, 34: 1510 -
8h
Lockwood MA.Clark JR.Parkin BC.Rothwell IP. Chem. Commun. 1996, 1973 - 9
Fujiwara Y.Moritani I.Danno S.Asano R.Teranishi S. J. Am. Chem. Soc. 1969, 91: 7166 - 10
Tsuji J. Palladium Reagents and Catalysts Wiley & Sons; New York: 1995. -
11a
Cope AC.Friedrich EC. J. Am. Chem. Soc. 1968, 90: 909 -
11b
van Helden R.Verberg G. Recl. Trav. Chim. Pays-Bas 1965, 84: 1263 - 12
Jia C.Kitamura T.Fujiwara Y. Acc. Chem. Res. 2001, 34: 633 -
13a
Jia C.Piao D.Oyamada J.Lu W.Kitamura T.Fujiwara Y. Science 2000, 287: 1992 -
13b
Lu W.Jia C.Kitamura T.Fujiwara Y. Org. Lett. 2000, 2: 2927 - 14
Stahl SS. Angew. Chem, Int. Ed. 2004, 43: 3400 - 15
Lafrance M.Rowley CN.Woo TK.Fagnou K. J. Am. Chem. Soc. 2006, 128: 8754 -
16a
García-Cuadrado D.Braga AAC.Maseras F.Echavarren AM. J. Am. Chem. Soc. 2006, 128: 1066 -
16b
Lafrance M.Fagnou K. J. Am. Chem. Soc. 2006, 128: 16496 -
16c
Davies DL.Donald SMA.Macgregor SA. J. Am. Chem. Soc. 2005, 127: 13754 -
17a
Dick AR.Kampf JW.Sanford MS. J. Am. Chem. Soc. 2005, 127: 12790 -
17b
Hull KL.Lanni EL.Sanford MS. J. Am. Chem. Soc. 2006, 128: 14047 - 18
Taylor R. Electrophilic Aromatic Substitution Wiley & Sons; New York: 1990. -
19a
Kalyani D.Deprez NR.Desai LV.Sanford MS. J. Am. Chem. Soc. 2005, 127: 7330 -
19b
Zaitsev VG.Shabashov D.Daugulis O. J. Am. Chem. Soc. 2005, 127: 13154 -
20a
Kawamura Y.Satoh T.Miura M.Nomura M. Chem. Lett. 1999, 961 -
20b
Satoh T.Kawamura Y.Miura M.Nomura M. Angew. Chem., Int. Ed. Engl. 1997, 36: 1740 -
20c
Daugulis O.Zaitsev VG. Angew. Chem. Int. Ed. 2005, 44: 4046 - 21
Hodgson HH. Chem. Rev. 1947, 40: 251 - 22
Nicolaou KC.Baran PS.Zhong Y.-L.Barluenga S.Hunt KW.Kranich R.Vega JA. J. Am. Chem. Soc. 2002, 124: 2233 -
23a
Horino H.Inoue N. J. Org. Chem. 1981, 46: 4416 -
23b
Tremont SJ.Rahman HU. J. Am. Chem. Soc. 1984, 106: 5759 -
23c
Wang Z.Zhang Z.Lu X. Organometallics 2000, 19: 775 -
23d
Zhang Z.Lu X.Xu Z.Zhang Q.Han X. Organometallics 2001, 20: 3724 -
24a
Boele MDK.van Strijdonck GPF.de Vries AHM.Kamer PCJ.de Vries JG.van Leeuwen PWNM. J. Am. Chem. Soc. 2002, 124: 1586 -
24b
Qang J.-R.Yang C.-T.Liu L.Guo Q.-X. Tetrahedron Lett. 2007, 48: 5449 - 25
Zaitsev VG.Daugulis O. J. Am. Chem. Soc. 2005, 127: 4156 - 26
Alberico D.Scott ME.Lautens M. Chem. Rev. 2007, 107: 174 -
27a
Hartwig JF. In Handbook of Organopalladium Chemistry for Organic SynthesisNegishi E.-i.de Meijere A. Wiley-Interscience; New York: 2002. p.1097 -
27b
Nicolaou KC.Bulger PG.Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4442 - 28
Butler A.Walker JV. Chem. Rev. 1993, 93: 1937 - 29
de la Mare PDB. Electrophilic Halogenation Cambridge University Press; New York: 1976. -
30a
Chen X.Li J.-J.Hao X.-S.Goodhue CE.Yu J.-Q. J. Am. Chem. Soc. 2006, 128: 78 -
30b
Dick AR.Hull KL.Sanford MS. J. Am. Chem. Soc. 2004, 126: 2300 - 31
Roy AH.Hartwig JF. J. Am. Chem. Soc. 2001, 123: 1232 - 32
Wan X.Ma Z.Li B.Zhang K.Cao S.Zhang S.Shi Z. J. Am. Chem. Soc. 2006, 128: 7416 -
33a
Hull KL.Anani WQ.Sanford MS. J. Am. Chem. Soc. 2006, 128: 7134 -
33b
Kalyani D.Dick AR.Anani WQ.Sanford MS. Org. Lett. 2006, 8: 2523 - 34
Chen X.Hao X.-S.Goodhue CE.Yu J.-Q. J. Am. Chem. Soc. 2006, 128: 6790 - 35
Hassan J.Se’vignon M.Gozzi C.Schulz E.Lemaire M. Chem. Rev. 2002, 102: 1359 - 36
Ritleng V.Sirlin C.Pfeffer M. Chem. Rev. 2002, 102: 1731 - 37
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 - 38
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 -
39a
Cho J.-Y.Tse MK.Holmes D.Maleczka RE.Smith MR. Science 2002, 295: 305 -
39b
Chotana GA.Rak MA.Smith MR. J. Am. Chem. Soc. 2005, 127: 10539 -
39c
Ishiyama T.Takagi J.Ishida K.Miyaura N.Anastasi N.Hartwig JF. J. Am. Chem. Soc. 2002, 124: 390 ; and references cited therein -
40a
Chen X.Goodhue CE.Yu J.-Q. J. Am. Chem. Soc. 2006, 128: 12634 -
40b
Giri R.Maugel N.Li J.-J.Wang D.-H.Breazzano SP.Saunders LB.Yu J.-Q. J. Am. Chem. Soc. 2007, 129: 3510 -
41a
Pastine SJ.Gribkov DV.Sames D. J. Am. Chem. Soc. 2006, 128: 14220 -
41b
Chatani N.Asaumi T.Yorimitsu S.Ikeda T.Kakiuchi F.Murai S. J. Am. Chem. Soc. 2001, 123: 10935 -
41c
Chatani N.Asaumi T.Ikeda T.Yorimitsu S.Ishii Y.Kakiuchi F.Murai S. J. Am. Chem. Soc. 2000, 122: 2882 - 42
Shi Z.Li B.Wan X.Cheng J.Fang Z.Cao B.Qin C.Wang Y. Angew. Chem. Int. Ed. 2007, 46: 5554 -
43a
Takahashi K.Minami T.Ohara Y.Hiyama T. Tetrahedron Lett. 1993, 34: 8263 -
43b
Alacid E.Najera C. Adv. Synth. Catal. 2006, 348: 945 -
43c
Katayama H.Nagao M.Ozawa F. J. Org. Chem. 2006, 71: 2699 -
43d
Pierrat P.Gros P.Fort Y. Org. Lett. 2005, 7: 697 -
44a
Hiyama T.Hatanaka Y. Pure Appl. Chem. 1994, 66: 1471 -
44b
Denmark SE.Sweis RF. Acc. Chem. Res. 2002, 35: 835 -
44c
Adam FL.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 - 45
Yang S.Li B.Wan X.Shi Z. J. Am. Chem. Soc. 2007, 129: 6066 -
46a
Hull KL.Lanni EL.Sanford MS. J. Am. Chem. Soc. 2006, 128: 14047 -
46b
Masui K.Ikegami H.Mori A. J. Am. Chem. Soc. 2004, 126: 5074 -
46c
Iataaki H.Yoshimoto H. J. Org. Chem. 1973, 38: 76 -
47a
Li Z.Li C.-J. J. Am. Chem. Soc. 2005, 127: 3672 -
47b
Li Z.Li C.-J. J. Am. Chem. Soc. 2005, 127: 6968 - 48
Li R.Jiang L.Lu W. Organometallics 2006, 25: 5973 - 49
Li B.-J.Tian S.-L.Fang Z.Shi Z.-J. Angew. Chem. Int. Ed. 2008, 47: 1115 -
50a
Stuart DR.Fagnou K. Science 2007, 316: 1172 -
50b
Stuart DR.Villemure E.Fagnou K. J. Am. Chem. Soc. 2007, 129: 12072 -
50c
Dwight TA.Rue NR.Charyk D.Josselyn R.DeBoef B. Org. Lett. 2007, 9: 3137 -
50d
Itahara T. J. Org. Chem. 1985, 50: 5272 - 51
Hull KL.Sanford MS. J. Am. Chem. Soc. 2007, 129: 11904 - 52
Knölker HJ.Reddy KR. Chem. Rev. 2002, 102: 4303 - 53
Tsang WCP.Zheng N.Buchwald SL. J. Am. Chem. Soc. 2005, 127: 14560 - 54
Chowdhury BK.Jha S. Synth. Commun. 2001, 31: 1559