Abstract
The unusual reactivity of novel bifunctional catalyst 1 in the selective isomerization of alkenes under mild conditions is reported. A variety of alkenes are converted to the (E)-isomer in excellent yield with low catalytic loading. Recent findings indicate that the reaction catalyzed by 1 is reversible, resulting in unusual kinetically controlled mixtures very rich in (E)-products.
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Trost BM, Kulawiec RJ (1993) J Am Chem Soc 115:2027
Slugovc C, Ruba E, Schmid R, Kirchner K (1999) Organometallics 18:4230
Kuznik N, Krompiec S (2007) Coord Chem Rev 25:222
Krompiec S, Krompiec M, Penczek R, Ignasiak H (2008) Coord Chem Rev 252:1819
Donohoe TJ, O’Riordan TJC, Rosa CP (2009) Angew Chem Int Ed 48:1014
Hanessian S, Giroux S, Larrson A (2006) Org Lett 8:5481
Stille JK, Becker Y (1980) J Org Chem 45:2139
Permin AB, Petrosyan VS (1990) Appl Organomet Chem 4:329
Yamamoto Y, Miyairi T, Ohmura T, Miyaura NJ (1999) J Org Chem 64:296
Ohmura T, Yamamoto Y, Miyaura N (1999) Organometallics 18:413
Suzuki H, Koyama Y, Moro-Oka Y, Ikawa T (1979) Tetrahedron Lett 20:1415
Epiotis ND, Bjorkquist D, Bjorkquist L, Sarkanen S (1973) J Am Chem Soc 95:7558
Kerrigan NJ, Bungard CJ, Nelson SG (2008) Tetrahedron 64:6863
Grotjahn DB, Larsen CR, Gustafson JL, Nair R, Sharma A (2007) J Am Chem Soc 129:9592
Grotjahn DB, Larsen CR, Erdogan G, Gustafson JL, Sharma A, Nair R (2009) Catal Org React 123:379
Erdogan G, Grotjahn DB (2009) J Am Chem Soc 131:10354
Lim H, Smith CR, RajanBabu TV (2009) J Org Chem 7:4565
Markovic D, Vogel P (2004) Angew Chem Int Ed 43:2928
Knorr R (1980) Chem Ber 113:2441
Acknowledgments
Dr. LeRoy Lafferty is thanked for his assistance with NMR experiments and the NSF for supporting this and related work.
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Larsen, C.R., Grotjahn, D.B. New Insights on Kinetic Versus Thermodynamic Ratios in Catalyzed Alkene Isomerization. Top Catal 53, 1015–1018 (2010). https://doi.org/10.1007/s11244-010-9572-y
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DOI: https://doi.org/10.1007/s11244-010-9572-y