Abstract
The nickelacyclic carboxylates A and B reacted with α-halo ketones to form α,β-unsaturated δ-ketocarboxylic acids which were easily converted into pyranones or isocoumarins. In addition, reaction of the nickelacyclic acyl derivative C with α-halo ketones resulted in the formation of substituted 1,3-dicarbonyl compounds with a benzoic acid substituent in the 1-position. In these reactions, many functional groups were tolerated.
Key words
cross coupling - metallacycles - organometallic reagents - nickel - heterocycles
References
1a Walther D.
Coord. Chem. Rev.
1987,
79:
135
1b Echavarren AM.
Castaño AM.
Adv. Metal-Org. Chem.
1998,
6:
1
1c Langer J.
Fischer R.
Görls H.
Walther D.
J. Organomet. Chem.
2004,
689:
2952
1d Castaño AM.
Echavarren AM.
Organometallics
1994,
13:
2262
1e Uhlig E.
Fehske G.
Nestler B.
Z. Anorg. Allg. Chem
1980,
465:
141
2a Fischer R.
Nestler B.
Schütz H.
Z. Anorg. Allg. Chem.
1989,
577:
11
2b Fischer R.
Walther D.
Bräunlich G.
Undeutsch B.
Ludwig W.
Bandmann H.
J. Organomet. Chem.
1992,
427:
395
2c Hoberg H.
Schaefer D.
Burkhart G.
J. Organomet. Chem.
1982,
228:
C21
2d Bräunlich G.
Fischer R.
Nestler B.
Walther D.
Z. Chem.
1989,
29:
417
2e Hoberg H.
Ballesteros A.
Sigan A.
Jégat C.
Milchereit A.
Synthesis
1991,
395
3a Schönecker B.
Walther D.
Fischer R.
Nestler B.
Bräunlich G.
Eibisch H.
Droeschler P.
Tetrahedron Lett.
1990,
31:
1257
3b Bräunlich G.
Walther D.
Eibisch H.
Schönecker B.
J. Organomet. Chem.
1993,
453:
295
3c Fischer R.
Schönecker B.
Walther D.
Synthesis
1993,
1267
4a Hoberg H.
Schaefer D.
Burkhart G.
Krüger C.
Romão MS.
J. Organomet. Chem.
1984,
266:
203
4b Yamamoto T.
Igarashi K.
Komiya S.
Yamamoto A.
J. Am. Chem. Soc.
1980,
102:
7448
4c Hoberg H.
Ballesteros A.
Sigan A.
Jégat C.
Bärhausen D.
Milchereit A.
J. Organomet. Chem.
1991,
407:
C23
5a Hoberg H.
Apotecher B.
J. Organomet. Chem.
1984,
270:
C15
5b Behr A.
Kanne U.
J. Organomet. Chem.
1986,
317:
C41
6a Castaño AM.
Echavarren AM.
Tetrahedron Lett.
1993,
34:
4361
6b Echavarren AM.
Castaño AM.
Tetrahedron
1995,
51:
2369
7a Hoberg H.
Peres Y.
Krüger C.
Tsay YT.
Angew. Chem.
1987,
99:
799
7b Hoberg H.
Schaefer D.
J. Organomet. Chem.
1982,
238:
383
7c Walther D.
Schönberg H.
Dinjus E.
Sieler J.
J. Organomet. Chem.
1987,
334:
377
7d Tsuda T.
Morikawa S.
Sumiya R.
Saegusa T.
J. Org. Chem.
1988,
53:
3140
7e Tsuda T.
Morikawa S.
Hasegawa N.
Saegusa T.
J. Org. Chem.
1990,
55:
2978
7f Walther D.
Bräunlich G.
Kempe R.
Sieler J.
J. Organomet. Chem.
1992,
436:
109
8a Takimoto M.
Mori M.
J. Am. Chem. Soc.
2001,
123:
2895
8b Takimoto M.
Mori M.
J. Am. Chem. Soc.
2002,
124:
10008
8c O’Brien EM.
Bercot EA.
Rovis T.
J. Am. Chem. Soc.
2003,
125:
10498
9a Napolitano E.
Org. Prep. Proced. Int.
1997,
29:
631
9b Tirodkar RB.
Usgaonkar RN.
Indian J. Chem.
1970,
8:
123
9c Hussain A.
Nasim H.
Muhammad T.
Malik A.
Indian J. Heterocycl. Chem.
1999,
8:
189
10 Hussain MT.
Rama NH.
Malik A.
Indian J. Chem., Sect. B
2001,
40:
372
11 Heller G.
Chem. Ber.
1935,
68:
1085
12 Rossi R.
Carpita A.
Bellina F.
Stabile P.
Mannina L.
Tetrahedron
2003,
59:
2067
13
COLLECT, Data Collection Software , Nonius B.V., Netherlands, 1998.
14 Otwinowski Z.
Minor W.
Processing of X-Ray Diffraction Data Collected in Oscillation Mode , In Methods in Enzymology
Vol. 276:
Carter CW.
Sweet RM.
Academic Press;
San Diego:
1997.
p.307-326
15 Sheldrick GM.
Acta Crystallogr., Sect. A
1990,
46:
467
16 Sheldrick, G. M. SHELXL-97 (Release 97-2), University of Göttingen, Germany, 1997.
17 CCDC-602921 (A ), CCDC-602922 (B ), CCDC-602923 (D ), CCDC-602924 (2a ), CCDC-602925 (2b′ ), CCDC-602926 (2c′ ), CCDC-602927 (2f′ ), CCDC-602928 (2g ), CCDC-602929 (2h′ ), CCDC-602930 (3a ), CCDC-602931 (3b ), CCDC-602932 (3d ), CCDC-602933 (3f ), CCDC-602934 (3g ), CCDC-602935 (3h′ ), CCDC-602936 (4f ), CCDC-602937 (4i ), CCDC-602938 (5a ), CCDC-602939 (5c ), CCDC-602940 (5g′ ) and CCDC-602941 (6 ) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK, fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk].
