Abstract
New complexes [Cp*Ru(bisimine)Cl] are
active catalysts for the regioselective alkylation of allylic carbonates
by soft carbonucleophiles, in favour of the branched isomers. The
catalysts can be conveniently prepared in situ from [Cp* Ru(cod)Cl] and
a bulky aromatic bisimine.
Keywords
regioselective allylic alkylation - ruthenium(bisimine) complex
catalysed - coupling reactions
References
1a
Trost BM.
van Vranken DL.
Chem. Rev.
1996,
96:
395
1b
Pfaltz A.
Lautens M. In
Comprehensive Asymmetric
Catalysis
Jacobsen EN.
Pfaltz A.
Yamamoto H.
Springer;
Berlin:
1999.
p.833
1c
Johansen M.
Jorgenssen KA.
Chem. Rev.
1998,
98:
1689
1d
Tsuji J. In
Transition Metal Reagents and Catalysts. Innovations
in Organic Synthesis
Wiley;
Chichester:
2000.
p.109
2a
Trost BM.
Acc. Chem. Res.
1996,
29:
355
2b
Kudis S.
Helmchen G.
Angew. Chem. Int. Ed.
1998,
37:
3047
2c
Pfaltz A.
Helmchen G.
Acc. Chem. Res.
2000,
33:
336
3a
Goux C.
Massacret M.
Lhoste P.
Sinou D.
Organometallics
1995,
14:
4585
3b
Trost BM.
Toste FD.
J.
Am. Chem. Soc.
1998,
120:
9074
3c
Blacker AJ.
Clarke ML.
Loft MS.
Williams JMJ.
Org.
Lett.
1999,
1:
1969
3d
Hayashi T.
Kawatsura M.
Uozumi Y.
J.
Am. Chem. Soc.
1998,
120:
1681
4a
Trost BM.
Tometzki GB.
Hung MH.
J.
Am. Chem. Soc.
1987,
109:
2176
4b
Lloyd-Jones GC.
Pfaltz A.
Angew. Chem.,
Int. Ed. Engl.
1995,
34:
462
4c
Trost BM.
Dogra K.
Hachiya I.
Emura T.
Hughes DL.
Krska S.
Reamer RA.
Palucki M.
Yasuda N.
Reider PJ.
Angew.
Chem. Int. Ed.
2002,
41:
1929
4d
Takeuchi R.
Ue N.
Tanabe K.
Yamashita K.
Shiga N.
J. Am. Chem. Soc.
2001,
123:
9525
4e
Bartels B.
Helmchen G.
Chem. Commun.
1999,
741
4f
Evans PA.
Kennedy LJ.
J.
Am. Chem. Soc.
2001,
123:
1234
4g
Blacker AJ.
Clarke ML.
Loft MS.
Williams JMJ.
Chem.
Commun.
1999,
913
4h
Kurosawa H.
J.
Chem. Soc., Dalton Trans.
1979,
939
4i
Brown JM.
MacIntyre JE.
J.
Chem. Soc., Perkin Trans. 2
1985,
961
5a
Minami I.
Shimizu I.
Tsuji J.
J. Organomet. Chem.
1985,
296:
269
5b
Zhang SW.
Mitsudo T.
Kondo T.
Watanabe Y.
J. Organomet.
Chem.
1993,
450:
197
5c
Zhang SW.
Mitsudo T.
Kondo T.
Watanabe Y.
J. Organomet
Chem.
1995,
485:
55
5d
Kondo T.
Ono H.
Satabe N.
Mitsudo T.
Watanabe Y.
Organometallics
1995,
14:
1945
5e
Trost BM.
Fraisse PL.
Ball ZT.
Angew. Chem. Int. Ed.
2002,
41:
1059
5f
Kang S.-K.
Kim D.-Y.
Hong R.-K.
Ho P.-S.
Synth. Commun.
1996,
26:
3225
5g
Matsushima Y.
Onitsuka K.
Kondo T.
Mitsudo T.
Takahashi SJ.
J.
Am. Chem. Soc.
2001,
123:
10405
6a
Le Paih J.
Dérien S.
Özdemir I.
Dixneuf PH.
J. Am. Chem. Soc.
2000,
122:
7400
6b
Le Paih J.
Dérien S.
Bruneau C.
Demerseman B.
Toupet L.
Dixneuf PH.
Angew. Chem. Int.
Ed.
2001,
40:
2912
6c
Le Paih J.
Dérien S.
Dixneuf PH.
Chem. Commun.
1999,
1437
7
Tsuji J.
Minami I.
Acc. Chem. Res.
1987,
20:
140
8 (C5 Me5 )RuCl(MesN=CH-CH=NMes):
selected 1 H NMR data (200 MHz): δ (ppm)
1.07 (s, 15 H, C5 Me5 ), 1.87 (s, 6 H, 2 Me),
2.30 (s, 6 H, 2 Me), 2.38 (s, 6 H, 2 Me), 6.82 (s, 2 H, 2 HAr),
6.92 (s, 2 H, 2 HAr), 8.68 (s, 2 H, 2 CH=N).