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Journal of the American Chemical Society
863-927; (2) Edmonds, M.; Abell, A. In Modern Carbonyl
catalyst is (moderately) recyclable. The interesting AIE
property of products arising from diene substrates makes
this protocol useful in novel material preparation. The
synthetic utility of this reaction is also demonstrated by the
synthesis of a deuterated trisubstituted alkene. Additionally,
a plausible catalytic cycle is proposed to rationalize the
mechanistic observations.
Olefination, Takeda, T. Ed; WileyVCH: Weinheim, 2004, pp 1-17.
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Catalyzed Olefin Isomerization Reactions. Synthesis 2019, 51,
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The Supporting Information is available free of charge on the
ACS Publications website.
Experimental details and spectra (PDF)
Crystallographic data (CCDC 1945169) (CIF)
AUTHOR INFORMATION
Corresponding Author
Authors
(6) For selected examples of noble metal-catalyzed alkene
isomerization: (a) Grotjahn, D. B.; Larsen, C. R.; Gustafson, J. L.; Nair,
Sheng Zhang orcid.org/0000-0002-9686-3921
R.; Sharma, A. Extensive Isomerization of Alkenes Using
a
Bifunctional Catalyst:ꢀ An Alkene Zipper. J. Am. Chem. Soc. 2007,
129, 9592-9593; (b) Erdogan, G.; Grotjahn, D. B. Mild and Selective
Deuteration and Isomerization of Alkenes by a Bifunctional
Catalyst and Deuterium Oxide. J. Am. Chem. Soc. 2009, 131, 10354-
10355; (c) Lim, H. J.; Smith, C. R.; RajanBabu, T. V. Facile Pd(II)- and
Ni(II)-Catalyzed Isomerization of Terminal Alkenes into 2-Alkenes.
J. Org. Chem. 2009, 74, 4565-4572; (d) Scarso, A.; Colladon, M.;
Sgarbossa, P.; Santo, C.; Michelin, R. A.; Strukul, G. Highly Active and
Selective Platinum(II)-Catalyzed Isomerization of Allylbenzenes:
Efficient Access to (E)-Anethole and Other Fragrances via Unusual
Agostic Intermediates. Organometallics 2010, 29, 1487-1497; (e)
Gauthier, D.; Lindhardt, A. T.; Olsen, E. P. K.; Overgaard, J.;
Skrydstrup, T. In Situ Generated Bulky Palladium Hydride
Complexes as Catalysts for the Efficient Isomerization of Olefins.
Selective Transformation of Terminal Alkenes to 2-Alkenes. J. Am.
Chem. Soc. 2010, 132, 7998-8009; (f) Larsen, C. R.; Grotjahn, D. B.
Stereoselective Alkene Isomerization over One Position. J. Am.
Chem. Soc. 2012, 134, 10357-10360; (g) Clark, J. R.; Griffiths, J. R.;
Diver, S. T. Ruthenium Hydride-Promoted Dienyl Isomerization:
Access to Highly Substituted 1,3-Dienes. J. Am. Chem. Soc. 2013,
135, 3327-3330; (h) Zhuo, L.-G.; Yao, Z.-K.; Yu, Z.-X. Synthesis of Z-
Alkenes from Rh(I)-Catalyzed Olefin Isomerization of β,γ-
Unsaturated Ketones. Org. Lett. 2013, 15, 4634-4637; (i) Larionov,
E.; Lin, L.; Guénée, L.; Mazet, C. Scope and Mechanism in Palladium-
Catalyzed Isomerizations of Highly Substituted Allylic,
Homoallylic, and Alkenyl Alcohols. J. Am. Chem. Soc. 2014, 136,
16882-16894; (j) Larsen, C. R.; Erdogan, G.; Grotjahn, D. B. General
Catalyst Control of the Monoisomerization of 1-Alkenes to trans-2-
Alkenes. J. Am. Chem. Soc. 2014, 136, 1226-1229; (k) Lin, L.;
Romano, C.; Mazet, C. Palladium-Catalyzed Long-Range
Deconjugative Isomerization of Highly Substituted α,β-
Unsaturated Carbonyl Compounds. J. Am. Chem. Soc. 2016, 138,
10344-10350; (l) Wang, Y.; Qin, C.; Jia, X.; Leng, X.; Huang, Z. An
Agostic Iridium Pincer Complex as a Highly Efficient and Selective
Catalyst for Monoisomerization of 1-Alkenes to trans-2-Alkenes.
Angew. Chem. Int. Ed. 2017, 56, 1614-1618; (m) Huang, R.-Z.; Lau,
K.-K.; Li, Z.-F.; Liu, T.-L.; Zhao, Y. Rhodium-Catalyzed
Notes
We are grateful to the National Science Foundation (CHE-
1554906) for their financial support.
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