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The two-electron reduction of 2,3-dimethylbuta-1,3-diene (DMB) with β-diketiminate and guanidinate substituted dimagnesium(I) compounds has given complexes in which two bidentate amido-magnesium fragments are bridged through the π-system of the DMB dianion, viz. [(LMg) 2 (μ-DMB)] (L= Xyl Nacnac, [HC(MeCNXyl) 2 ] - , Xyl=2,6-xylyl; or Priso=[(DipN) 2 CNPr i 2 ] - , Dip=2,6-diisopropylphenyl). Similar double reductions of [4]dendralene (4dend) have afforded the complexes, [(LMg) 2 (μ-4dend)] (L= Ar Nacnac, Ar=Xyl or mesityl (Mes); or Priso) in which the 4dend dianion is π-coordinated to the bidentate amido-magnesium fragments. Treatment of several such complexes with THF leads to Z- to E-isomerization of the dendralene fragment, and formation of purely σ-bonded Mg-C interactions in the THF coordinated products [{( Ar Nacnac)(THF)Mg} 2 (μ-4dend)] (Ar=Xyl, Mes or Dip). Reaction of myrcene (Myr) with [{( Xyl Nacnac)Mg} 2 ] proceeds via reductive coupling of Myr to give a previously unknown acyclic, branched C 20 tetra-olefin dianion complex [{( Xyl Nacnac)(THF)Mg} 2 (μ-Myr) 2 ]. Preliminary reactions of [(LMg) 2 (μ-DMB)] with H 2 and/or CO yielded a series of products, including novel magnesium hydride compounds, products derived from couplings of CO with the reduced DMB fragment (viz. magnesium dimethylcyclohexadienediolates), and one magnesium cyclopropanetriolate complex from the magnesium(I) induced coupling of DMB with H 2 and CO.

Titel:	Reductive Metallation of Dendralenes and Myrcene Using Dimagnesium(I) Compounds: A Facile Route to Unsaturated Organomagnesium Compounds.
Autor/in / Beteiligte Person:	Mullins, JC ; Yuvaraj, K ; Sowden, MJ ; Sherburn, MS ; Jones, C
Link:	Full Text Finder (Volltext)
Zeitschrift:	Chemistry (Weinheim an der Bergstrasse, Germany), Jg. 30 (2024-01-26), Heft 6, S. e202303219
Veröffentlichung:	Weinheim, Germany : Wiley-VCH, 2024
Medientyp:	academicJournal
ISSN:	1521-3765 (electronic)
DOI:	10.1002/chem.202303219
Sonstiges:	Nachgewiesen in: MEDLINE Sprachen: English Publication Type: Journal Article Language: English [Chemistry] 2024 Jan 26; Vol. 30 (6), pp. e202303219. <i>Date of Electronic Publication: </i>2023 Dec 07. References: See for example:. ; H. Hopf, M. S. Sherburn, Angew. Chem. Int. Ed. 2012, 51, 2298-2338;. ; H. Hopf, G. Maas, in The Chemistry of Dienes and Polyenes, Vol. 1 (Ed.: Z. Rappoport), Wiley, Chichester, 1997. ; M. S. Sherburn, Acc. Chem. Res. 2015, 48, 1961-1970. ; Y. M. Fan, M. J. Sowden, N. L. Magann, E. J. Lindeboom, M. G. Gardiner, M. S. Sherburn, J. Am. Chem. Soc. 2022, 144, 20090-20098. ; A. D. Payne, G. Bojase, M. N. Paddon-Row, M. S. Sherburn, Angew. Chem. Int. Ed. 2009, 48, 4836-4839. ; H. Toombs-Ruane, N. Osinski, T. Fallon, C. Wills, A. C. Willis, M. N. Paddon-Row, M. S. Sherburn, Chem. Asian J. 2011, 6, 3243-3250. ; See for example:. ; S. S. Wreford, J. F. Whitney, Inorg. Chem. 1981, 20, 3918-3924;. ; M. G. Gardiner, C. L. Raston, F. G. N. Cloke, P. B. Hitchcock, Organometallics 1985, 14, 1339-1353;. ; Y. Kai, N. Kanehisa, K. Miki, N. Kasai, K. Mashima, H. Yasuda, A. Nakamura, Chem. Lett. 1982, 11, 1277-1280. ; See for example: W. J. Evans, D. G. Giarikos, C. B. Robledo, V. S. Leong, J. W. Ziller, Organometallics 2001, 20, 5648-5652. ; S. P. Green, C. Jones, A. Stasch, Science 2007, 318, 1754-1756. ; . ; C. Jones, Nat. Chem. Rev. 2017, 1, 0059;. ; C. Jones, Commun. Chem. 2020, 3, 159. ; A. J. Boutland, A. Carroll, C. A. Lamsfus, A. Stasch, L. Maron, C. Jones, J. Am. Chem. Soc. 2017, 139, 18190-18193. ; K. Yuvaraj, I. Douair, L. Maron, C. Jones, Chem. Eur. J. 2020, 26, 14665-14670. ; . ; D. Dange, A. R. Gair, D. D. L. Jones, M. Juckel, S. Aldridge, C. Jones, Chem. Sci. 2019, 10, 3208-3216;. ; R. Y. Kong, M. R. Crimmin, J. Am. Chem. Soc. 2020, 142, 11967-11971;. ; F. Rekhroukh, L. Zhang, R. Y. Kong, A. J. P. White, M. R. Crimmin, Chem. Commun. 2022, 58, 8282-8285. ; A. Behr, L. Johnen, ChemSusChem 2009, 2, 1072-1095. ; A. J. Edwards, R. O. Piltz, G. Frenking, A. Stasch, C. Jones, Nat. Commun. 2018, 9, 3079. ; M. A. G. M. Tinga, G. Schat, O. S. Akkerman, F. Bickelhaupt, E. Horn, H. Kooijman, W. J. J. Smeets, A. L. Spek, J. Am. Chem. Soc. 1993, 115, 2808-2817. ; . ; J. Hicks, M. Juckel, A. Paparo, D. Dange, C. Jones, Organometallics 2018, 37, 4810-4813;. ; S. J. Bonyhady, C. Jones, S. Nembenna, A. Stasch, A. J. Edwards, G. J. McIntyre, Chem. Eur. J. 2010, 16, 938-955. ; As determined from a survey of the Cambridge Crystallographic Database, August, 2023. ; K. Yuvaraj, C. Jones, Chem. Commun. 2021, 57, 9224-9227. ; See for example:. ; H. Bauer, S. Harder in Homogeneous Hydrogenation with Non-Precious Catalysts, first edition, J. J. Teichart (ed.), Wiley-VCH, Weinhiem, p.p. 141-165, 2020;. ; Y. Liang, U. K. Das, J. Luo, Y. Diskin-Posner, L. Avram, D. Milstein, J. Am. Chem. Soc. 2022, 144, 19115-19126. ; R. Lalrempuia, C. E. Kefalidis, S. J. Bonyhady, B. Schwarze, L. Maron, A. Stasch, C. Jones, J. Am. Chem. Soc. 2015, 137, 8944-8947. ; S. J. Bonhady, D. Collis, G. Frenking, N. Holzmann, C. Jones, A. Stasch, Nat. Chem. 2010, 2, 865-869. ; G. Jin, C. Jones, P. C. Junk, K.-A. Lippert, R. P. Rose, A. Stasch, New J. Chem. 2009, 33, 64-75. ; N. B. A related coupling of DMB with CO to give a cyclohexadienediolate at a zirconium center has been reported. T. N. Valadez, J. R. Norton, M. C. Neary, P. J. Quinlivan, Organometallics 2016, 35, 3163-3169. ; C. Jones, M. Ma, A. Stasch, Chem. Eur. J. 2012, 18, 10669-10676. ; T. M. McPhillips, S. McPhillips, H. J. Chiu, A. E. Cohen, A. M. Deacon, P. J. Ellis, E. Garman, A. Gonzalez, N. K. Sauter, R. P. Phizackerley, S. M. Soltis, P. Kuhn, J. Synchrotron Radiat. 2002, 9, 401-406. ; W. J. Kabsch, J. Appl. Crystallogr. 1993, 26, 795-800. ; G. M. Sheldrick, SHELX-16, University of Göttingen, 2016. Grant Information: Australian Research Council; FA2386-21-1-4048 Air Force Office of Scientific Research Contributed Indexing: Keywords: carbon monoxide; dendralene; hydrogenation; magnesium(I); myrcene; reduction Entry Date(s): Date Created: 20231121 Latest Revision: 20240128 Update Code: 20240129

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Reductive Metallation of Dendralenes and Myrcene Using Dimagnesium(I) Compounds: A Facile Route to Unsaturated Organomagnesium Compounds.