Communication
Palladium‐Catalyzed Allylic Substitution at Four‐Membered‐Ring Systems: Formation of η1‐Allyl Complexes and Electrocyclic Ring Opening†
†
We are grateful to the Max‐Planck‐Society and the Max‐Planck‐Institut für Kohlenforschung for generous support of our research programs. This work was funded by the ERC (Starting Grant 278872 to N.M.). The invaluable support of our NMR, HPLC, and GC departments as well as Dr. R. Goddard (MPI Mülheim) for crystallographic analysis, is acknowledged. L.G.A. and A.M.M. are grateful to FCT, Portugal (SFRH/BD/44295/2008 and PEst‐OE/QUI/UI0100/2011) for financial support.
Abstract
Caught in the act: A series of unique η1‐allyl palladium complexes of four‐membered cyclic systems bearing β‐hydrogens were prepared (see structure). Their unusual structure, reactivity, and unprecedented propensity for undergoing pericyclic reactions were uncovered.
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- Peter Polák, Tomáš Tobrman, Novel Selective Approach to Terminally Substituted [n]Dendralenes, European Journal of Organic Chemistry, 10.1002/ejoc.201801522, 2019, 5, (957-968), (2018).
- Qiu-Chao Mu, Jing Chen, Chun-Gu Xia, Li-Wen Xu, Synthesis of silacyclobutanes and their catalytic transformations enabled by transition-metal complexes, Coordination Chemistry Reviews, 10.1016/j.ccr.2018.06.015, 374, (93-113), (2018).
- Stefan Pusch, Dieter Schollmeyer, Till Opatz, Synthesis and Unusual NMR‐Spectroscopic Behavior of a Strained Bicyclic Ammonium Salt, European Journal of Organic Chemistry, 10.1002/ejoc.201701594, 2018, 10, (1204-1207), (2017).
- Jianyou Mao, Jiadi Zhang, Hui Jiang, Ana Bellomo, Mengnan Zhang, Zidong Gao, Spencer D. Dreher, Patrick J. Walsh, Palladium‐Catalyzed Asymmetric Allylic Alkylations with Toluene Derivatives as Pronucleophiles, Angewandte Chemie, 10.1002/ange.201509917, 128, 7, (2572-2576), (2016).
- Jianyou Mao, Jiadi Zhang, Hui Jiang, Ana Bellomo, Mengnan Zhang, Zidong Gao, Spencer D. Dreher, Patrick J. Walsh, Palladium‐Catalyzed Asymmetric Allylic Alkylations with Toluene Derivatives as Pronucleophiles, Angewandte Chemie International Edition, 10.1002/anie.201509917, 55, 7, (2526-2530), (2016).
- Antonio Misale, Supaporn Niyomchon, Nuno Maulide, Cyclobutenes: At a Crossroad between Diastereoselective Syntheses of Dienes and Unique Palladium-Catalyzed Asymmetric Allylic Substitutions, Accounts of Chemical Research, 10.1021/acs.accounts.6b00375, 49, 11, (2444-2458), (2016).
- Zi‐Qiang Rong, Min Wang, Chi Hao Eugene Chow, Yu Zhao, A Catalyst‐Enabled Diastereodivergent Aza‐Diels–Alder Reaction: Complementarity of N‐Heterocyclic Carbenes and Chiral Amines, Chemistry – A European Journal, 10.1002/chem.201601626, 22, 28, (9483-9487), (2016).
- Caroline Souris, Antonio Misale, Yong Chen, Marco Luparia, Nuno Maulide, From Stereodefined Cyclobutenes to Dienes: Total Syntheses of Ieodomycin D and the Southern Fragment of Macrolactin A, Organic Letters, 10.1021/acs.orglett.5b02149, 17, 18, (4486-4489), (2015).
- Lan-Gui Xie, Viktor Bagutski, Davide Audisio, Larry M. Wolf, Volker Schmidts, Kathrin Hofmann, Cornelia Wirtz, Walter Thiel, Christina M. Thiele, Nuno Maulide, Dynamic behaviour of monohaptoallylpalladium species: internal coordination as a driving force in allylic alkylation chemistry, Chemical Science, 10.1039/C5SC01867F, 6, 10, (5734-5739), (2015).
- Stefan A. Ruider, Tobias Sandmeier, Erick M. Carreira, Total Synthesis of (±)‐Hippolachnin A, Angewandte Chemie International Edition, 10.1002/anie.201410419, 54, 8, (2378-2382), (2014).
- Stefan A. Ruider, Tobias Sandmeier, Erick M. Carreira, Total Synthesis of (±)‐Hippolachnin A, Angewandte Chemie, 10.1002/ange.201410419, 127, 8, (2408-2412), (2014).
- Mei Xiang, Nan Li, R. Bruce King, Henry F. Schaefer III, Metal triangles versus metal chains and terminal versus bridging hydrogen atoms in trinuclear osmium carbonyl hydride chemistry, New J. Chem., 10.1039/C3NJ01479G, 38, 4, (1433-1440), (2014).
- Larry M. Wolf, Walter Thiel, Origin of Inversion versus Retention in the Oxidative Addition of 3-Chloro-cyclopentene to Pd(0)L n , The Journal of Organic Chemistry, 10.1021/jo5020068, 79, 24, (12136-12147), (2014).
- Antonio Misale, Supaporn Niyomchon, Marco Luparia, Nuno Maulide, Asymmetrische Palladium‐katalysierte allylische Alkylierung mit Dialkylzinkreagentien: ein bemerkenswerter Ligandeneffekt, Angewandte Chemie, 10.1002/ange.201309074, 126, 27, (7188-7193), (2014).
- Walter Thiel, Katalyseforschung auf dem Computer, Angewandte Chemie, 10.1002/ange.201402118, 126, 33, (8748-8757), (2014).
- Manfred T. Reetz, 100 Jahre Max‐Planck‐Institut für Kohlenforschung, Angewandte Chemie, 10.1002/ange.201403217, 126, 33, (8702-8727), (2014).
- Antonio Misale, Supaporn Niyomchon, Marco Luparia, Nuno Maulide, Asymmetric Palladium‐Catalyzed Allylic Alkylation Using Dialkylzinc Reagents: A Remarkable Ligand Effect, Angewandte Chemie International Edition, 10.1002/anie.201309074, 53, 27, (7068-7073), (2014).
- Walter Thiel, Computational Catalysis—Past, Present, and Future, Angewandte Chemie International Edition, 10.1002/anie.201402118, 53, 33, (8605-8613), (2014).
- Manfred T. Reetz, One Hundred Years of the Max‐Planck‐Institut für Kohlenforschung, Angewandte Chemie International Edition, 10.1002/anie.201403217, 53, 33, (8562-8586), (2014).
- Heinz‐Maier‐Leibnitz‐Preis: N. Maulide / Karl‐Ziegler‐Gastprofessur: D. Enders / EurJIC Young Investigator Prize: K. Ray, Angewandte Chemie, 10.1002/ange.201306179, 125, 40, (10609-10609), (2013).
- Heinz Maier‐Leibnitz Prize: N. Maulide / Karl Ziegler Guest Professorship: D. Enders / EurJIC Young Investigator Prize: K. Ray, Angewandte Chemie International Edition, 10.1002/anie.201306179, 52, 40, (10417-10417), (2013).
