Abstract
Ready accessible 2-trifluoromethanesulfonyloxyindole-1-carboxylic acid ethyl ester undergoes palladium-catalyzed coupling reactions with different partners giving rise to 2-aryl, heteroaryl, vinyl, allyl, and alkynyl indoles in good to excellent yields.
Key words
indoles - palladium-catalyzed - boronic acids/esters - alkynes - heteroarylzinc chlorides
References
1a
Abbiati G.
Beccalli E.
Marchesini A.
Rossi E.
Synthesis
2001,
2477
1b
Beccalli E.
Broggini G.
Marchesini A.
Rossi E.
Tetrahedron
2002,
58:
6673
1c
Abbiati G.
Arcadi A.
Beccalli E.
Rossi E.
Tetrahedron Lett.
2003,
44:
5331
1d
Abbiati G.
Arcadi A.
Bellinazzi A.
Beccalli E.
Rossi E.
Zanzola S.
J. Org. Chem.
2005,
70:
4088
1e
Abbiati G.
Canevari V.
Rossi E.
Ruggeri A.
Synth. Commun.
2005,
35:
1845
2
Tsuji J.
Palladium Reagents and Catalysts Innovation in Organic Synthesis
Wiley;
Chichester:
1995.
3
Bergman J.
Venemalm L.
J. Org. Chem.
1992,
57:
2495
4a
Kline T.
J. Heterocycl. Chem.
1985,
505
4b
Vazquez E.
Davies IW.
Payack JF.
J. Org. Chem.
2002,
67:
7551
5a
Perez-Serrano L.
Casarrubios L.
Dominguez G.
Gonzalez-Perez P.
Perez-Castells J.
Synthesis
2002,
1810
5b
Prikhod’ko TA.
Kurilenko VM.
Khlienko ZhN.
Vasilevskii SF.
Shvartsberg MS.
Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.)
1990,
120
5c
Passarella D.
Lesma G.
Deleo M.
Martinelli M.
Silvani A.
J. Chem. Soc., Perkin Trans. 1
1999,
2669
5d
Sakamoto T.
Numata A.
Saitoh H.
Kondo Y.
Chem. Pharm. Bull.
1999,
1740
5e
Passarella D.
Giardini A.
Martinelli M.
Silvani A.
J. Chem. Soc., Perkin Trans. 1
2001,
127
6a
Merlic CA.
McInnes DM.
Tetrahedron Lett.
1997,
38:
7661
6b
Merlic CA.
You Y.
McInnes DM.
Zechman AL.
Miller MM.
Deng Q.
Tetrahedron
2001,
57:
5199
7
Conway SC.
Gribble GW.
Synth. Commun.
1992,
2987
8
Bourlot AS.
Desarbe E.
Mérour JY.
Synthesis
1994,
411
9
Benoît J.
Malapel B.
Mérour JY.
Synth. Commun.
1996,
3289
10
Johnson CN.
Stemp G.
Anand N.
Stephen SC.
Gallagher T.
Synlett
1998,
1025
11a
Sakamoto T.
Kondo Y.
Takazawa N.
Yamanaka H.
J. Chem. Soc., Perkin Trans. 1
1996,
1927
11b
Danieli B.
Lesma G.
Martinelli M.
Passarella D.
Peretto I.
Silvani A.
Tetrahedron
1998,
54:
14081
12a
Labadie SS.
Teng E.
J. Org. Chem.
1994,
59:
4250
12b
Palmisano G.
Santagostino M.
Helv. Chim. Acta
1993,
76:
2356
13 We synthesized the trifluoromethanesulfonic acid 1-trifluoromethanesulfonyl-1H -indol-2-yl ester 3 from 1,3-dihydroindol-2-one(5 ) in 70% yield following the procedure described by Gribble.7 However, 3 is stable only at low temperatures and after reaction with phenylacetylene or with 2-methyl-3-butyn-2-ol under Sonogashira conditions at 60 °C, the corresponding coupled products were isolated in poor yields (31% and 32%, respectively).
14
Porcs-Makkay M.
Argay G.
Kálmán A.
Simig G.
Tetrahedron
2000,
56:
5893
15
Johnson AT.
Klein ES.
Wang L.
Pino ME.
Chandraratna RAS.
J. Med. Chem.
1996,
39:
5027