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
<A NAME="RZ13905SS-1A">1a </A>
Abbiati G.
Beccalli E.
Marchesini A.
Rossi E.
Synthesis
2001,
2477
<A NAME="RZ13905SS-1B">1b </A>
Beccalli E.
Broggini G.
Marchesini A.
Rossi E.
Tetrahedron
2002,
58:
6673
<A NAME="RZ13905SS-1C">1c </A>
Abbiati G.
Arcadi A.
Beccalli E.
Rossi E.
Tetrahedron Lett.
2003,
44:
5331
<A NAME="RZ13905SS-1D">1d </A>
Abbiati G.
Arcadi A.
Bellinazzi A.
Beccalli E.
Rossi E.
Zanzola S.
J. Org. Chem.
2005,
70:
4088
<A NAME="RZ13905SS-1E">1e </A>
Abbiati G.
Canevari V.
Rossi E.
Ruggeri A.
Synth. Commun.
2005,
35:
1845
<A NAME="RZ13905SS-2">2 </A>
Tsuji J.
Palladium Reagents and Catalysts Innovation in Organic Synthesis
Wiley;
Chichester:
1995.
<A NAME="RZ13905SS-3">3 </A>
Bergman J.
Venemalm L.
J. Org. Chem.
1992,
57:
2495
<A NAME="RZ13905SS-4A">4a </A>
Kline T.
J. Heterocycl. Chem.
1985,
505
<A NAME="RZ13905SS-4B">4b </A>
Vazquez E.
Davies IW.
Payack JF.
J. Org. Chem.
2002,
67:
7551
<A NAME="RZ13905SS-5A">5a </A>
Perez-Serrano L.
Casarrubios L.
Dominguez G.
Gonzalez-Perez P.
Perez-Castells J.
Synthesis
2002,
1810
<A NAME="RZ13905SS-5B">5b </A>
Prikhod’ko TA.
Kurilenko VM.
Khlienko ZhN.
Vasilevskii SF.
Shvartsberg MS.
Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.)
1990,
120
<A NAME="RZ13905SS-5C">5c </A>
Passarella D.
Lesma G.
Deleo M.
Martinelli M.
Silvani A.
J. Chem. Soc., Perkin Trans. 1
1999,
2669
<A NAME="RZ13905SS-5D">5d </A>
Sakamoto T.
Numata A.
Saitoh H.
Kondo Y.
Chem. Pharm. Bull.
1999,
1740
<A NAME="RZ13905SS-5E">5e </A>
Passarella D.
Giardini A.
Martinelli M.
Silvani A.
J. Chem. Soc., Perkin Trans. 1
2001,
127
<A NAME="RZ13905SS-6A">6a </A>
Merlic CA.
McInnes DM.
Tetrahedron Lett.
1997,
38:
7661
<A NAME="RZ13905SS-6B">6b </A>
Merlic CA.
You Y.
McInnes DM.
Zechman AL.
Miller MM.
Deng Q.
Tetrahedron
2001,
57:
5199
<A NAME="RZ13905SS-7">7 </A>
Conway SC.
Gribble GW.
Synth. Commun.
1992,
2987
<A NAME="RZ13905SS-8">8 </A>
Bourlot AS.
Desarbe E.
Mérour JY.
Synthesis
1994,
411
<A NAME="RZ13905SS-9">9 </A>
Benoît J.
Malapel B.
Mérour JY.
Synth. Commun.
1996,
3289
<A NAME="RZ13905SS-10">10 </A>
Johnson CN.
Stemp G.
Anand N.
Stephen SC.
Gallagher T.
Synlett
1998,
1025
<A NAME="RZ13905SS-11A">11a </A>
Sakamoto T.
Kondo Y.
Takazawa N.
Yamanaka H.
J. Chem. Soc., Perkin Trans. 1
1996,
1927
<A NAME="RZ13905SS-11B">11b </A>
Danieli B.
Lesma G.
Martinelli M.
Passarella D.
Peretto I.
Silvani A.
Tetrahedron
1998,
54:
14081
<A NAME="RZ13905SS-12A">12a </A>
Labadie SS.
Teng E.
J. Org. Chem.
1994,
59:
4250
<A NAME="RZ13905SS-12B">12b </A>
Palmisano G.
Santagostino M.
Helv. Chim. Acta
1993,
76:
2356
<A NAME="RZ13905SS-13">13 </A>
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).
<A NAME="RZ13905SS-14">14 </A>
Porcs-Makkay M.
Argay G.
Kálmán A.
Simig G.
Tetrahedron
2000,
56:
5893
<A NAME="RZ13905SS-15">15 </A>
Johnson AT.
Klein ES.
Wang L.
Pino ME.
Chandraratna RAS.
J. Med. Chem.
1996,
39:
5027