A.M. Zawisza, J. Muzart / Catalysis Communications 12 (2011) 1015–1017
1017
[
6] For a review of Heck reactions of allylic alcohols, see:. J. Muzart, Tetrahedron 61
2005) 4179–4212.
OH
NH
OH
(
Cl
[7] Z.D. Petrović, S. Marković, D. Simijonović, V. Petrović, Monatsh. Chem. 140 (2009)
371–374.
[
Cs CO
3
O
N
N
PdCl2
2
NH Pd HN
Cl
Pd
8] Z.D. Petrović, M.I. Djuran, F.W. Heinemann, S. Rajković, S.R. Trifunivić, Bioorg.
Chem. 34 (2006) 225–234.
9] S. Marković, Z.D. Petrović, V. Petrović, Monatsh. Chem. 140 (2009) 171–175.
THF, rt
CH Cl , rt
2
2
O
[
9
10
HO
[10] In the reports referenced in [9] and [11], 3 was drawn and/or written without the
negative charge.
Scheme 5. Neutral palladium complexes from PdCl
2
and L-prolinol.
[11] Z.D. Petrović, V.P. Petrović, D. Simijonović, S. Marković, J. Organomet. Chem. 694
(2009) 3852–3858.
[
[
12] G.M. Kapteijn, P.J. Baesjou, P.L. Alsters, D.M. Grove, W.J.J. Smeets, H. Kooijman, A.L.
Spek, G. van Koten, Chem. Ber. Recl. 130 (1997) 35–44.
13] I. Warad, A. Al-Warthan, S. Al-Reseyes, N. Al-Zaqri, M. Fattoh, M. Al-Kahtani,
Arabian J. Chem. 1 (2008) 161–169.
Pd(OAc) (0.05 equiv.)
amino alcohol (0.1 equiv.)
2
NaHCO (1.1 equiv.)
3
Ph
[14] F. Accadbled, B. Tinant, E. Hénon, D. Carrez, A. Croisy, S. Bouquillon, Dalton Trans.
PhX
+
R
R
39 (2010) 8982–8993.
DMF, 120 °C, 16 h
[
[
15] a) T. Nishimura, T. Onoue, K. Ohe, S. Uemura, J. Org. Chem. 64 (1999) 6750–6755;
b) J. Muzart, Tetrahedron 59 (2003) 5789–5816.
16] a) W.A. Herrmann, C. Brossmer, K. Öfele, C.P. Reisinger, T. Priermeier, M. Beller, H.
Fischer, Angew. Chem. Int. Ed. 34 (1995) 1844–1847;
9
9
a: X = I
b: X = Br
10a: R = Ph
11a: R = Ph
11b: R = CO Et
10b: R = CO Et
2
2
Scheme 6. Palladium-catalyzed intermolecular phosphine-free Heck reactions.
b) M. Beller, T.H. Riermeier, Tetrahedron Lett. 37 (1996) 6535–6538;
c) B.L. Shaw, 22, New J. Chem. 22 (1998) 77–798 and 649;
d) B.L. Shaw, Chem. Commun. (1998) 1361–1362;
e) F. Miyazaki, K. Yamaguchi, M. Shibasaki, Tetrahedron Lett. 40 (1999)
7379–7383;
Table 1
Heck reactions.
a
f) A.S. Gruber, D. Zim, G. Ebeling, A.L. Monteiro, J. Dupont, Org. Lett. 2 (2002)
Entry
9
10
Amino alcohol
Product
Yield %a,b
Yield %b,c
1287–1290;
g) D. Tsvelikhovsky, I. Popov, V. Gutkin, A. Rozin, A. Shvartsman, J. Blum, Eur. J.
Org. Chem. (2009) 98–102;
h) J. Aydin, J.M. Larsson, N. Selander, K.J. Szabó, Org. Lett. 11 (2009) 2852–2854.
17] a) W.A. Herrmann, V.P.W. Böhm, C.P. Reisinger, J. Organomet. Chem. 576 (1999)
1
2
3
4
5
9a
9a
9a
9a
9b
10a
10b
10a
10b
10a
(+)-cinchonine
(+)-cinchonine
(−)-ephedrine
(−)-ephedrine
(+)-cinchonine
11a
11b
11a
11b
11a
89
98
83
98
43
75
80
75
80
82
[
23–41;
b) N.J. Whitcombe, K.K. Hii, S.E. Gibson, Tetrahedron 57 (2001) 7449–7476.
II
IV
a
[18] According to computational studies, the Pd /Pd mechanism would be feasible
either if a weakly coordinating ligand is present: A. Sundermann, O. Uzan, J.M.L.
Martin, Chem. Eur. J. 7 (2001) 1703–17118 or using pincer-type palladium
complexes:
Isolated yield under conditions depicted in Scheme 6.
Only the trans product was detected from 1H NMR analysis.
Isolated yield at 110 °C using 2 as the catalyst and HN(CH CH
b
c
2
2
OH)
2
as the base [7].
O. Blacque, C.M. Frech, Chem. Eur. J. 16 (2010) 1521–1531.
[
19] a) R. McCrindle, G. Ferguson, G.J. Arsenault, A.J. McAlees, J. Chem. Soc. Chem.
Commun. (1983) 571–572;
Acknowledgements
b) V.V. Grushin, H. Alper, Organometallics 12 (1993) 1890–1901;
c) A.M. Trzeciak, Z. Ciunik, J.J. Ziołkowski, Organometallics 21 (2002) 132–137;
d) A.A. Pletnev, Q. Tian, R.C. Larock, J. Org. Chem. 67 (2002) 9276–9287;
e) J. Le Bras, D.K. Mukherjee, S. González, M. Tristany, B. Ganchegui, M. Moreno-
Mañas, R. Pleixats, F. Henin, J. Muzart, New J. Chem. 28 (2004) 1550–1553.
We are grateful to Prof. J. Gal (University of Colorado) for
correspondence.
References
[20] For a review, see: J. Mol. Catal. A Chem. 308 (2009) 15–24.
21] R.F. Heck, J.P. Nolley, J. Org. Chem. 37 (1972) 2320–2322.
[
[
1] a) F. Hénin, J. Muzart, Tetrahedron Asymmetr. 3 (1992) 1161–1164;
b) J. Muzart, F. Hénin, S. Jamal Aboulhoda, Tetrahedron Asymmetr. 8 (1997)
[22] a) C.G. Pierpont, R.M. Buchanan, H.H. Downs, J. Organomet. Chem. 124 (1977)
103–112;
3
81–389;
b) L. Canovese, F. Visentin, P. Uguagliati, B. Crociani, J. Chem. Soc. Dalton Trans.
(1996) 1921–1926;
c) O. Roy, A. Riahi, F. Hénin, J. Muzart, Eur. J. Org. Chem. (2002) 3986–3994;
d) J.-F. Detalle, A. Riahi, V. Steinmetz, F. Hénin, J. Muzart, J. Org. Chem. 69 (2004)
c) R. Fernández-Galánd, F.A. Jalón, B.R. Manzano, J. Rodríguez de-la Fuente,
Organometallics 16 (1997) 3758–3768;
6528–6532.
[
2] The term unichiral, which refers to chiral compounds consisting of a single
enantiomer, has been proposed by Gal: J. Gal, Enantiomer 3 (1998) 263–2738 The
term homochiral has not to be used for such compounds:
d) R.A. Klein, P. Witte, R. van Belzen, J. Fraanje, K. Goubitz, M. Numan, H. Schenk,
J.M. Ernsting, C.J. Elsevier, Eur. J. Inorg. Chem. (1998) 319–330;
e) K.M. Dawood, M.S. Fayed, M.M. Elkhalea, ARKIVOC xiii (2010) 324–341.
[23] T. Borkowski, A.M. Trzeciak, W. Bukowski, A. Bukowska, W. Tylus, L. Kępiński,
Appl. Catal. A 378 (2010) 83–89.
[24] W. Yang, C. Liu, J. Qiu, Chem. Commun. 46 (2010) 2659–2661.
2
[25] Very recently, Petrović's team has reported improved yields using PdCl in ionic
liquids based on diethanolamine: Z.D. Petrović, D. Simijonović, V.P. Petrović, S.
Marković, J. Mol. Catal. A Chem. 327 (2010) 45–50.
[26] Concomitantly to the acceptation of our manuscript, once more [7, 9] DFT study
a) J. Gal, J. Chromatogr. A 829 (1998) 417–418;
b) E.L. Eliel, S.H. Wilen, L.N. Mander, Stereochemistry of Organic Compounds,
Wiley, New York, 1993, p. 12008, For the definition of homochirality, see also:
D.G. Blackmond, Angew. Chem. Int. Ed. 48 (2009) 2648–2654.
3] S. Bouquillon, A. du Moulinet d'Hardemare, M.-T. Averbuch-Pouchot, F. Hénin, J.
Muzart, A. Durif, Acta Crystallogr. C C55 (1999) 2028–2030.
4] S. Bouquillon, S. Humbel, U. Létinois-Halbes, F. Hénin, J. Muzart, J. Organomet.
Chem. 687 (2003) 377–383.
5] A.M. Zawisza, B. Ganchegui, I. González, S. Bouquillon, A. Roglans, F. Hénin, J.
Muzart, J. Mol. Catal. A: Chem. 283 (2008) 140–145.
[
[
[
from Petrović's team on the formation of
2 2 2 2 2
3 from PdCl [NH(CH CH OH) ]
appeared in the literature: V.P. Petrović, S. Marković, Z.D. Petrović, Monatsh.
Chem. 142 (2011) 141–144.