Manjunath Lamani et al.
COMMUNICATIONS
Na2SO4, the solvent was removed under reduced pressure to
afford the reduced product 2e as a pale yellow liquid; yield:
91 mg (85%). IR (neat): n=2965, 1489, 1243, 1071, 977,
J. A. Krause, C. Bruckner, Org. Biomol. Chem. 2010, 8,
1951; e) J. F. Teichert, B. L. Feringa, Synlett 2010, 1200;
f) C. Singh, A. S. Singh, N. K. Naikade, V. P. Verma, M.
Hassam, N. Gupta, S. Pandey, Synlett 2010, 1014;
g) J. D. White, J. Yang, Synlett 2009, 1713; h) D. P.
Dickson, C. Toh, M. Lunda, M. V. Yermolina, D. J War-
drop, C. L. Landrie, J. Org. Chem. 2009, 74, 9535;
i) M. E. Jung, G. J. Im, J. Org. Chem. 2009, 74, 8739;
j) T. J. Donohoe, R. M. Harris, O. Williams, G. C. Har-
gaden, J. Burrows, J. Parker, J. Am. Chem. Soc. 2009,
131, 12854; k) J. R. Harris, S. R. Waetzig, K. A. Woer-
pel, Org. Lett. 2009, 11, 3290; l) H. Fuwa, K. Ishigai, T.
Goto, A. Suzuki, M. Sasaki, J. Org. Chem. 2009, 74,
4024; m) T. Yoshikawa, S. Mori, M. Shindo, J. Am.
Chem. Soc. 2009, 131, 2092; n) C. L. Morris, Y. Hu,
G. D. Head, L. J. Brown, W. G. Whittingham, R. C. D.
Brown, J. Org. Chem. 2009, 74, 981; o) I. Ortin, J. F.
Gonzalez, E. De. La. Cuesta, C. Avendano, Tetrahe-
dron 2009, 65, 2201; p) A. Auvinet, B. Eignerova, A.
Guy, M. Kotora, T. Durand, Tetrahedron Lett. 2009, 50,
1498; q) A. Dondoni, A. Marra, Tetrahedron Lett. 2009,
50, 3593; r) Y. Murakami, M. Yoshida, K. Shishido, Tet-
rahedron Lett. 2009, 50, 1279; s) J. F. Teichert, T. D.
Hartog, M. Hanstein, C. Smit, B. T. Horst, V. Hernan-
dez-Olmos, B. L. Feringa, A. J. Minnaard, ACS Catal.
2011, 1, 309; t) C. Gaviglio, F. Doctorovich, J. Org.
Chem. 2008, 73, 5379.
821 cmÀ1
;
1H NMR (CDCl3, 400 MHz): d=7.34 (d, J=
8.9 Hz, 2H), 6.76 (d, J=8.9 Hz, 2H), 3.86 (t, J=6.5 Hz,
2H), 1.83–1.74 (m, 2H), 1.02 (t, J=7.3 Hz, 3H); 13C NMR
(CDCl3, 100 MHz): d=158.21, 132.14, 116.27, 112.52, 69.7,
22.46, 10.43; anal. calcd. for C9H12O; C 50.26, H 5.15;
found: C 50.61, H 5.47.
Acknowledgements
This work was supported by ARMREB, New-Delhi
(ARMREB/EMCB/2009/111), the Indian Institute of Science
and RL fine Chem. The authors thank Dr. A. R. Ramesha
and Prof. S. Chandrasekhar for useful discussion. ML thanks
CSIR, New-Delhi for a senior research fellowship.
References
[1] P. A. Chaloner, M. A. Esteruelas, F. Joo, L. A. Oro, Ho-
mogeneous Hydrogenation, Kluwer Academic Publish-
ers, Dordrecht, The Netherlands, 1994.
[2] a) G. Zassinovich, G. Mestroni, S. Gladiali, Chem. Rev.
1992, 92, 1051; b) R. Noyori, S. Hashiguchi, Acc. Chem.
Res. 1997, 30, 97; c) J. W. Yang, M. T. H. Fonseca, B.
List, Angew. Chem. 2004, 116, 6829; Angew. Chem. Int.
Ed. 2004, 43, 6660; d) S. G. Ouellet, J. B. Tuttle,
D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 32;
e) J. W. Yang, M. T. H. Fonseca, N. Vignola, B. List,
Angew. Chem. 2005, 117, 110; Angew. Chem. Int. Ed.
2005, 44, 108; f) M. Rueping, J. Dufour, F. R. Schoepke,
Green Chem. 2011, 13, 1084.
[9] a) R. C. Ebersole, F. C. Chang, J. Org. Chem. 1973, 38,
2579; b) B. M. Trost, S. Schneider, J. Am. Chem. Soc.
1989, 111, 4430; c) W. R. Roush, L. K. Hoong, M. A. J.
Palmer, J. A. Straub, A. D. Palkowitz, J. Org. Chem.
1990, 55, 4117.
[10] a) Y. Jang, S. Kim, S. W. Jun, B. H. Kim, S. Hwang,
I. K. Song, B. M. Kim, T. Hyeon, Chem. Commun.
2011, 47, 3601; b) E. Kim, S. Kim, B. M. Kim, Bull.
Korean Chem. Soc. 2011, 32, 3183.
[11] Surprisingly, the reduction of styrene 1a in an oxygen
atmosphere resulted in a low yield of the reduced prod-
uct 2a (40%) under similar reduction conditions.
[12] a) D. B. Denney, R. R. Dileone, J. Am. Chem. Soc.
1962, 84, 4737; b) M. Paul; R. Jean-Claude, J. Chem.
Soc. Perkin Trans. 2 2000, 2232.
[13] Reduction of a 1:1 mixture of cis- and trans-stilbene
under the standard reaction conditions (1. 5 equiv. of
aqueous hydrazine) showed that the trans isomer is
more susceptible for the reaction furnishing the re-
duced product along with unreacted cis- and trans-stil-
bene in the ratio of 3:2.
[3] Handbook of Homogeneous Hydrogenation, (Ed.: J. G.
de Vries, C. J. Elsevier), Wiley-VCH, New York, 2007.
[4] H. S. Wilkinson, R. Hett, G. J. Tanoury, C. H. Sena-
nayake, S. A. Wald, Org. Process Res. Dev. 2000, 4, 567.
[5] For reviews on hydrazine as reducing agent see: a) S.
Hꢂnig, H. R. Muller, W. Thier, Angew. Chem. 1965, 77,
368; Angew. Chem. Int. Ed. Engl. 1965, 4, 271; b) D. J.
Pasto, R. T. Taylor, Org. React. 1991, 40, 91.
[6] a) S. K. Singh, X.-B. Zhang, Q. Xu, J. Am. Chem. Soc.
2009, 131, 9894; b) S. K. Singh, Q. Xu, J. Am. Chem.
Soc. 2009, 131, 18032, and references cited therein.
[7] a) Y. Imada, H. Iida, T. Naota, J. Am. Chem. Soc. 2005,
127, 14544; b) C. Smit, M. W. Fraaije, A. J. Minnaard, J.
Org. Chem. 2008, 73, 9482; c) B. J. Marsh, D. R. Carb-
ery, J. Org. Chem. 2009, 74, 3186; d) Y. Imada, T. kita-
gawa, T. Ohno, H. Iida, T. Naota, Org. Lett. 2010, 12,
32; e) B. J. Marsh, E. L. Heath, D. R. Carbery, Chem.
Commun. 2011, 47, 280; f) Y. Imada, H. Iida, T. kitaga-
wa, T. Naota, Chem. Eur. J. 2011, 17, 5908; g) K. R.
Buszek, N. Brown, J. Org. Chem. 2007, 72, 3125.
[14] L. D. Field, H. Li, S. Dalgarno, P. Turner, Chem.
Commun. 2008, 1680.
[15] However, formation of the intermediate II could not
be ascertained.
[16] Similarly, in the reduction experiment of styrene (1a)
with aqueous hydrazine (1.5 equiv.) and FeCl3·6H2O
(5 mol%), isolating the reduced product (2a), the white
residue was reused for the second and third runs for re-
duction of styrene (1a) in the presence of aqueous hy-
drazine (1.5 equiv.). As observed in the recycling ex-
periment (Table 4), the second run furnished a good
yield of the reduced product 2a (99%), whereas the
third run resulted in low yield of the reduced product
(2a) (55%).
[8] For recent examples of diimide mediated olefin reduc-
tion: a) S. E. Denmark, N. S. Werner, J. Am. Chem.
Soc. 2010, 132, 3612; b) C. D. Smith, J. I. Gavrilyuk,
A. J. Lough, R. A. Batey, J. Org. Chem. 2010, 75, 702;
c) C. W. Wullschleger, J. Gertsch, K. Altmann, Org.
Lett. 2010, 12, 1120; d) L. P. Samankumara, M. Zeller,
1442
ꢀ 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2012, 354, 1437 – 1442