Organic Letters
Details experimental procedures and characterization for
Letter
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(7) (a) Bezier, D.; Park, S.; Brookhart, M. Org. Lett. 2013, 15, 496−
499. (b) Feghali, E.; Jacquet, O.; Thuery, P.; Cantat, T. Catal. Sci.
́
Technol. 2014, 4, 2230−2234.
(8) Zheng, J.; Chevance, S.; Darcel, C.; Sortais, J.-B. Chem. Commun.
2013, 49, 10010−10012.
AUTHOR INFORMATION
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(9) (a) Wang, C.; Yang, X. Chem. - Asian J. 2018, 13, 2307−2315.
(b) Trovitch, R. J. Acc. Chem. Res. 2017, 50, 2842−2852. (c) Trovitch,
R. J. Synlett 2014, 25, 1638−1642. (d) Royo, B. Recent advances in
catalytic hydrosilylation of carbonyl groups mediated by well-defined
first-row late transition metals. In Advances in Organometallic
Chemistry; Academic Press: 2019.
Corresponding Author
ORCID
Notes
(10) Kallmeier, F.; Kempe, R. Angew. Chem., Int. Ed. 2018, 57, 46−
60.
(11) (a) Harms, R. G.; Herrmann, W. A.; Kuhn, F. E. Coord. Chem.
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Rev. 2015, 296, 1−23. (b) Kuninobu, Y.; Takai, K. Chem. Rev. 2011,
111, 1938−1953.
The authors declare no competing financial interest.
(12) (a) Kennedy-Smith, J. J.; Nolin, K. A.; Gunterman, H. P.;
Toste, F. D. J. Am. Chem. Soc. 2003, 125, 4056−4057. (b) Nolin, K.
A.; Krumper, J. R.; Pluth, M. D.; Bergman, R. G.; Toste, F. D. J. Am.
Chem. Soc. 2007, 129, 14684−14696. (c) Nolin, K. A.; Ahn, R. W.;
Toste, F. D. J. Am. Chem. Soc. 2005, 127, 12462−12463. (d) Nolin, K.
A.; Krumper, J. R.; Pluth, M. D.; Bergman, R. G.; Toste, F. D. J. Am.
Chem. Soc. 2007, 129, 14684−14696. (e) Nolin, K. A.; Ahn, R. W.;
Kobayashi, Y.; Kennedy-Smith, J. J.; Toste, F. D. Chem. - Eur. J. 2010,
16, 9555−9562.
ACKNOWLEDGMENTS
We thank the Centre National de la Recherche Scientifique
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(CNRS), the Universite de Rennes 1, the Universite Toulouse
III, Paul Sabatier, and the Institut Universitaire de France
̈
(IUF) for general support of this project and Noel Lugan for
his support. R.B. is grateful to the Embassy of Yemen in Paris,
and the program Pause for financial support.
(13) (a) Ison, E. A.; Trivedi, E. R.; Corbin, R. A.; Abu-Omar, M. M.
J. Am. Chem. Soc. 2005, 127, 15374−15375. (b) Du, G.; Abu-Omar,
M. M. Organometallics 2006, 25, 4920−4923. (c) Ison, E. A.;
Cessarich, J. E.; Du, G.; Fanwick, P. E.; Abu-Omar, M. M. Inorg.
Chem. 2006, 45, 2385−2387. (d) Du, G.; Fanwick, P. E.; Abu-Omar,
M. M. J. Am. Chem. Soc. 2007, 129, 5180−5187. (e) Du, G.; Abu-
Omar, M. M. Curr. Org. Chem. 2008, 12, 1185−1198. (f) Du, G.;
Fanwick, P. E.; Abu-Omar, M. M. Inorg. Chim. Acta 2008, 361, 3184−
REFERENCES
■
(1) (a) Cha, J. S.; Kim, J. E.; Lee, K. W. J. Org. Chem. 1987, 52,
5030−5032. (b) Cha, J. S.; Kim, J. E.; Oh, S. Y. Bull. Korean Chem.
Soc. 1987, 8, 313−318. (c) Yokoyama, T.; Yamagata, N. Appl. Catal.,
A 2001, 221, 227−239. (d) Bedenbaugh, A. O.; Bedenbaugh, J. H.;
Bergin, W. A.; Adkins, J. D. J. Am. Chem. Soc. 1970, 92, 5774−5775.
(e) Muraki, M.; Mukaiyama, T. Chem. Lett. 1974, 3, 1447−1450.
(f) Hubert, T. D.; Eyman, D. P.; Wiemer, D. F. J. Org. Chem. 1984,
49, 2279−2281. (g) Cha, J. S.; Lee, K. D.; Kwon, O. O.; Kim, J. M.;
Lee, H. S. Bull. Korean Chem. Soc. 1995, 16, 561−565. (h) Brown, H.
C.; Cha, J. S.; Nazer, B.; Yoon, N. M. J. Am. Chem. Soc. 1984, 106,
8001−8002. (i) Brown, H. C.; Cha, J. S.; Yoon, N. M.; Nazer, B. J.
Org. Chem. 1987, 52, 5400−5406. (j) Marlett, E. M.; Park, W. S. J.
Org. Chem. 1990, 55, 2968−2969. (k) Sato, F.; Jinbo, T.; Sato, M.
Synthesis 1981, 1981, 871−871. (l) Corriu, R. J. P.; Lanneau, G. F.;
Perrot, M. Tetrahedron Lett. 1987, 28, 3941−3944.
3192. (g) Royo, B.; Romao
107−112.
̃
, C. C. J. Mol. Catal. A: Chem. 2005, 236,
(14) Toh, C. K.; Sum, Y. N.; Fong, W. K.; Ang, S. G.; Fan, W. Y.
Organometallics 2012, 31, 3880−3887.
(15) (a) Wei, D.; Roisnel, T.; Darcel, C.; Clot, E.; Sortais, J.-B.
ChemCatChem 2017, 9, 80−83. (b) Li, H.; Wei, D.; Bruneau-Voisine,
A.; Ducamp, M.; Henrion, M.; Roisnel, T.; Dorcet, V.; Darcel, C.;
́
Carpentier, J.-F.; Soule, J.-F.; Sortais, J.-B. Organometallics 2018, 37,
1271−1279. (c) Wei, D.; Sadek, O.; Dorcet, V.; Roisnel, T.; Darcel,
C.; Gras, E.; Clot, E.; Sortais, J.-B. J. Catal. 2018, 366, 300−309.
(2) Trost, B. M. Comprehensive Organic Synthesis; Pergamon: Oxford,
1991; Vol. 8, pp 259−305.
́
(d) Zheng, J.; Elangovan, S.; Valyaev, D. A.; Brousses, R.; Cesar, V.;
Sortais, J.-B.; Darcel, C.; Lugan, N.; Lavigne, G. Adv. Synth. Catal.
2014, 356, 1093−1097. (e) Valyaev, D. A.; Wei, D.; Elangovan, S.;
Cavailles, M.; Dorcet, V.; Sortais, J.-B.; Darcel, C.; Lugan, N.
Organometallics 2016, 35, 4090−4098.
(3) (a) Zhang, M.; Li, N.; Tao, X.; Ruzi, R.; Yu, S.; Zhu, C. Chem.
Commun. 2017, 53, 10228−10231. (b) Sakai, N.; Minato, K.;
Ogiwara, Y. Tetrahedron Lett. 2017, 58, 4563−4567. (c) Tokuyama,
H.; Yokoshima, S.; Yamashita, T.; Shao-Cheng, L.; Leping, L.;
Fukuyama, T. J. Braz. Chem. Soc. 1998, 9, 381−387. (d) Braden, R.;
Himmler, T. J. Organomet. Chem. 1989, 367, C12−C14. (e) Fukuya-
ma, T.; Lin, S. C.; Li, L. J. Am. Chem. Soc. 1990, 112, 7050−7051.
(f) Four, P.; Guibe, F. J. Org. Chem. 1981, 46, 4439−4445. (g) Ho, P.
T.; Ngu, K. Y. J. Org. Chem. 1993, 58, 2313−2316. (h) Chandrasekhar,
S.; Kumar, M. S.; Muralidhar, B. Tetrahedron Lett. 1998, 39, 909−910.
(i) Kangani, C. O.; Kelley, D. E.; Day, B. W. Tetrahedron Lett. 2006,
47, 6289−6292. (j) Gutsulyak, D. V.; Nikonov, G. I. Adv. Synth. Catal.
2012, 354, 607. (k) Fujisawa, T.; Mori, T.; Tsuge, S.; Sato, T.
Tetrahedron Lett. 1983, 24, 1543−1546. (l) Nagayama, K.; Shimizu,
I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2001, 74, 1803−1815.
(m) Gooßen, L. J.; Ghosh, K. Chem. Commun. 2002, 836−837.
(n) Gooßen, L. J.; Khan, B. A.; Fett, T.; Treu, M. Adv. Synth. Catal.
2010, 352, 2166−2170. (o) Fujihara, T.; Cong, C.; Terao, J.; Tsuji, Y.
Adv. Synth. Catal. 2013, 355, 3420−3424.
́
(16) Tehfe, M.-A.; Lalevee, J.; Gigmes, D.; Fouassier, J. P. J. Polym.
Sci., Part A: Polym. Chem. 2010, 48, 1830−1837.
(17) In all cases, the selectivity 2:3 was above 94:6.
(18) The reduction of crotonic (1y) and 3-methylcrotonic (1z)
acids led after hydrolysis to butanal (5y) and 3-methylbutanal (5z) in
82% and 91% yield, respectively; see SI.
(19) Liquid 3-phenylpropionaldehyde slowly evolved towards solid
2,4,6-tri(2-phenylethyl)-1,3,5-trioxane after purification.
(4) Addis, D.; Das, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed.
2011, 50, 6004−6011.
(5) Miyamoto, K.; Motoyama, Y.; Nagashima, H. Chem. Lett. 2012,
41, 229−231.
(6) Misal Castro, L. C.; Li, H.; Sortais, J.-B.; Darcel, C. Chem.
Commun. 2012, 48, 10514−10516.
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