The Aluminyl Anion: A New Generation of Aluminium Nucleophile.
aluminium
aluminyl
main group
nucleophile
organometallic
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
25 01 2021
25 01 2021
Historique:
received:
25
05
2020
pubmed:
23
6
2020
medline:
23
6
2020
entrez:
23
6
2020
Statut:
ppublish
Résumé
Trivalent aluminium compounds are well known for their reactivity as Lewis acids/electrophiles, a feature that is exploited in many pharmaceutical, industrial and laboratory-based reactions. Recently, a series of isolable aluminium(I) anions ("aluminyls") have been reported, which offer an alternative to this textbook description: these reagents behave as aluminium nucleophiles. This minireview covers the synthesis, structure and reactivity of aluminyl species reported to date, together with their associated metal complexes. The frontier orbitals of each of these species have been investigated using a common methodology to allow for a like-for-like comparison of their electronic structure and a means of rationalising (sometimes unprecedented) patterns of reactivity.
Identifiants
pubmed: 32567755
doi: 10.1002/anie.202007530
doi:
Types de publication
Journal Article
Review
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1702-1713Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
CRC Handbook of Chemistry and Physics (Ed.: W. M. Haynes), 97th ed., CRC Press, Boca Raton, FL, 2016, pp. 14-17.
Bauxite to Alumina: The Bayer Process. An Introductory Text (Ed.: A. Bagshaw), 2017.
The Group 13 Metals Aluminium, Gallium, Indium and Thallium: Chemical Patterns and Peculiarities (Eds.: S. Aldridge, A. J. Downs), Wiley, Chichester, 2011.
S. Saito in Main Group Metals in Organic Synthesis (Eds.: H. Yamamoto, K. Oshima), Wiley-VCH, Weinheim, 2004, pp. 189-306;
P. A. Chaloner in The Metal-Carbon Bond (Ed.: F. R. Hartley), Wiley, New York, 1987, pp. 411-472;
T. Ooi, K. Maruoka in Lewis Acids in Organic Synthesis (Ed.: H. Yamamoto), Wiley-VCH, Weinheim, 2000, pp. 191-281.
M. S. Hill in Low Oxidation State Chemistry. Encyclopedia of Inorganic and Bioinorganic Chemistry, Wiley, Hoboken, 2015, pp. 1-18;
P. Bag, C. Weetman, S. Inoue, Angew. Chem. Int. Ed. 2018, 57, 14394-14413;
Angew. Chem. 2018, 130, 14594-14613;
A. Schnepf, H. Schnöckel, Angew. Chem. Int. Ed. 2002, 41, 3532-3552;
Angew. Chem. 2002, 114, 3682-3704 and references therein.
W. Uhl, Angew. Chem. Int. Ed. Engl. 1993, 32, 1386-1397;
Angew. Chem. 1993, 105, 1449-1461;
C. Dohmeier, D. Loos, H. Schnöckel, Angew. Chem. Int. Ed. Engl. 1996, 35, 129-149;
Angew. Chem. 1996, 108, 141-161.
W. Klemm, E. Voss, K. Z. Geiersberger, Z. Anorg. Allg. Chem. 1948, 256, 15-24;
P. J. Durrant, B. Durrant, Introduction to Advanced Inorganic Chemistry, Prentice Hall Press, London, 1972;
M. Mocker, C. Robl, H. Schnöckel, Angew. Chem. Int. Ed. Engl. 1994, 33, 1754-1755;
Angew. Chem. 1994, 106, 1860-1861;
A. Ecker, H. Schnöckel, Z. Anorg. Allg. Chem. 1996, 622, 149-152;
H. J. Himmel, J. Bahlo, M. Haussmann, F. Kurth, G. Stösser, H. Schnöckel, Inorg. Chem. 2002, 41, 4952-4960;
M. Tacke, H. Schnöckel, Inorg. Chem. 1989, 28, 2895-2896.
C. Dohmeier, C. Robl, M. Tacke, H. Schnöckel, Angew. Chem. Int. Ed. Engl. 1991, 30, 564-565;
Angew. Chem. 1991, 103, 594-595.
S. Schulz, H. W. Roesky, H. J. Koch, G. M. Sheldrick, D. Stalke, A. Kuhn, Angew. Chem. Int. Ed. Engl. 1993, 32, 1729-1731;
Angew. Chem. 1993, 105, 1828-1830.
C. Cui, H. W. Roesky, H.-G. Schmidt, M. Noltemeyer, H. Hao, F. Cimpoesu, Angew. Chem. Int. Ed. 2000, 39, 4274-4276;
Angew. Chem. 2000, 112, 4444-4446.
Y. Lui, J. Li, X. Ma, Z. Yang, H. W. Roesky, Coord. Chem. Rev. 2018, 374, 387-415.
C. Bakewell, M. Garçon, R. Y. Kong, L. O'Hare, A. J. P. White, M. R. Crimmin, Inorg. Chem. 2020, 59, 4608-4616;
A. Dmitrienko, J. F. Britten, D. Spasyuk, G. I. Nikonov, Chem. Eur. J. 2020, 26, 206-211;
C. Bakewell, A. J. P. White, M. R. Crimmin, Chem. Sci. 2019, 10, 2452-2458;
L. L. Liu, J. Zhou, L. L. Cao, D. W. Stephan, J. Am. Chem. Soc. 2019, 141, 16971-16982;
S. Sinhababu, M. M. Siddiqui, S. K. Sarkar, A. Münch, R. Herbst-Irmer, A. George, P. Parameswaran, D. Stalke, H. W. Roesky, Chem. Eur. J. 2019, 25, 11422-11426;
A. Paparo, C. D. Smith, C. Jones, Angew. Chem. Int. Ed. 2019, 58, 11459-11463;
Angew. Chem. 2019, 131, 11581-11585;
A. Koner, B. M. Gabidullin, Z. Kelemen, L. Nyulászi, G. I. Nikonov, R. Streubel, Dalton Trans. 2019, 48, 8248-8253;
C. Bakewell, B. J. Ward, A. J. P. White, M. R. Crimmin, Chem. Sci. 2018, 9, 2348-2356;
S. Brand, H. Elsen, J. Langer, W. A. Donaubauer, F. Hampel, S. Harder, Angew. Chem. Int. Ed. 2018, 57, 14169-14173;
Angew. Chem. 2018, 130, 14365-14369;
R. Y. Kong, M. R. Crimmin, J. Am. Chem. Soc. 2018, 140, 13614-13617;
S. Sinhababu, S. Kundu, A. N. Paesch, R. Herbst-Irmer, D. Stalke, H. W. Roesky, Eur. J. Inorg. Chem. 2018, 2237-2240;
C. Bakewell, A. J. P. White, M. R. Crimmin, Angew. Chem. Int. Ed. 2018, 57, 6638-6642;
Angew. Chem. 2018, 130, 6748-6752;
L. Tuscher, C. Helling, C. Wölper, W. Frank, A. S. Nizovtsev, S. Schulz, Chem. Eur. J. 2018, 24, 3241-3250;
T. N. Hooper, M. Garçon, A. J. P. White, M. R. Crimmin, Chem. Sci. 2018, 9, 5435-5440.
P. Bag, A. Porzelt, P. J. Altmann, S. Inoue, J. Am. Chem. Soc. 2017, 139, 14384-14387.
S. K. Mellerup, Y. Cui, F. Fantuzzi, P. Schmid, J. T. Goettel, G. Bélanger-Chabot, M. Arrowsmith, I. Krummenacher, Q. Ye, V. Engel, B. Engels, H. Braunschweig, J. Am. Chem. Soc. 2019, 141, 16954-16960.
A. Hofmann, C. Pranckevicius, T. Tröster, H. Braunschweig, Angew. Chem. Int. Ed. 2019, 58, 3625-3629;
Angew. Chem. 2019, 131, 3664-3668.
We use the term “aluminyl” to refer to systems containing the formally anionic AlX2− fragment, based on well established literature precedent for the related derivatives of other group 13 elements: that is, boryl, gallyl and indyl for the boron, gallium and indium analogues. Although the terms boranyl, alumanyl, gallanyl and indiganyl are recommended by the IUPAC red book (R. M. Hartshorn, A. T. Hutton in Nomenclature of Inorganic Chemistry, IUPAC Recommendations 2005, IUPAC Red Book, (Eds.: N. G. Connelly, T. Damhus), RSC Publishing, London, 2005) for the parent BH2, AlH2, GaH2 and InH2 systems, this convention has not been followed in the naming of previous boron, gallium or indium systems of the types BX2−, GaX2− and InX2−.
E. S. Schmidt, A. Jockisch, H. Schmidbaur, J. Am. Chem. Soc. 1999, 121, 9758-9759.
R. J. Baker, R. D. Farley, C. Jones, M. Kloth, D. M. Murphy, J. Chem. Soc. Dalton Trans. 2002, 3844-3850;
I. L. Fedushkin, A. N. Lukoyanov, G. K. Fukin, S. Y. Ketkov, M. Hummert, H. Schumann, Chem. Eur. J. 2008, 14, 8465-8468.
R. J. Baker, C. Jones, Coord. Chem. Rev. 2005, 249, 1857-1869;
M. Asay, C. Jones, M. Driess, Chem. Rev. 2011, 111, 354-396.
Y. Segawa, M. Yamashita, K. Nozaki, Science 2006, 314, 113-115.
Y. Segawa, Y. Suzuki, M. Yamashita, K. Nozaki, J. Am. Chem. Soc. 2008, 130, 16069-16079.
L. Weber, Eur. J. Inorg. Chem. 2017, 3461-3488.
W. Lu, H. Hu, Y. Li, R. Ganguly, R. Kinjo, J. Am. Chem. Soc. 2016, 138, 6650-6661;
A.-F. Pécharman, A. L. Colebatch, M. S. Hill, C. L. McMullin, M. F. Mahon, C. Weetman, Nat. Commun. 2017, 8, 15022.
R. J. Schwamm, M. D. Anker, M. Lein, M. P. Coles, C. M. Fitchett, Angew. Chem. Int. Ed. 2018, 57, 5885-5887;
Angew. Chem. 2018, 130, 5987-5989;
M. D. Anker, Y. Altaf, M. Lein, M. P. Coles, Dalton Trans. 2019, 48, 16588-16594.
M. D. Anker, M. Lein, M. P. Coles, Chem. Sci. 2019, 10, 1212-1218.
B. E. Cole, J. P. Wolbach, W. G. Dougherty, Jr., N. A. Piro, W. S. Kassel, C. R. Graves, Inorg. Chem. 2014, 53, 3899-3906;
A. Hinchliffe, F. S. Mair, E. J. L. McInnes, R. G. Pritcharda, J. E. Warren, Dalton Trans. 2008, 222-233;
Y. Zhao, Y. Liu, B. Wu, X.-J. Yang, Dalton Trans. 2015, 44, 13671-13680.
J. Hicks, P. Vasko, J. M. Goicoechea, S. Aldridge, Nature 2018, 557, 92-95.
A third example of a diamido aluminyl anion was reported by Harder and co-workers whilst this manuscript was under review-see S. Harder, S. Grams, J. Eyselein, J. Langer, C. Färber, Angew. Chem. Int. Ed. 2020, https://doi.org/10.1002/anie.202006693;
Angew. Chem. 2020, https://doi.org/10.1002/ange.202006693.
R. J. Schwamm, M. D. Anker, M. Lein, M. P. Coles, Angew. Chem. Int. Ed. 2019, 58, 1489-1493;
Angew. Chem. 2019, 131, 1503-1507.
R. J. Schwamm, M. P. Coles, M. S. Hill, M. F. Mahon, C. L. McMullin, N. A. Rajabi, A. S. S. Wilson, Angew. Chem. Int. Ed. 2020, 59, 3928-3932;
Angew. Chem. 2020, 132, 3956-3960.
J. Hicks, P. Vasko, J. M. Goicoechea, S. Aldridge, J. Am. Chem. Soc. 2019, 141, 11000-11003.
S. Kurumada, S. Takamori, M. Yamashita, Nat. Chem. 2020, 12, 36-39.
K. Koshino, R. Kinjo, J. Am. Chem. Soc. 2020, 142, 9057-9062.
B. Cordero, V. Gómez, A. E. Platero-Prats, M. Revés, J. Echeverría, E. Cremades, F. Barragán, S. Alvarez, Dalton Trans. 2008, 2832-2838.
D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39-92.
D. Martin, N. Lassauque, B. Donnadieu, G. Bertrand, Angew. Chem. Int. Ed. 2012, 51, 6172-6175;
Angew. Chem. 2012, 124, 6276-6279.
J. Hicks, A. Mansikkamäki, P. Vasko, J. M. Goicoechea, S. Aldridge, Nat. Chem. 2019, 11, 237-241.
K. Sugita, M. Yamashita, Chem. Eur. J. 2020, 26, 4520-4523.
A. Heilmann, J. Hicks, P. Vasko, J. M. Goicoechea, S. Aldridge, Angew. Chem. Int. Ed. 2020, 59, 4897-4901;
Angew. Chem. 2020, 132, 4927-4931.
J. J. Cabrera-Trujillo, I. Fernandez, Chem. Eur. J. 2020, https://doi.org/10.1002/chem.202000921.
K. Sugita, R. Nakano, M. Yamashita, Chem. Eur. J. 2020, 26, 2174-2177.
M. Anker, M. P. Coles, Angew. Chem. Int. Ed. 2019, 58, 13452-13455;
Angew. Chem. 2019, 131, 13586-13589.
M. Anker, C. L. McMullin, N. A. Rajabi, M. P. Coles, Angew. Chem. Int. Ed. 2020, https://doi.org/10.1002/anie.202005301;
Angew. Chem. 2020, https://doi.org/10.1002/ange.202005301.
J. Hicks, A. Heilmann, P. Vasko, J. M. Goicoechea, S. Aldridge, Angew. Chem. Int. Ed. 2019, 58, 17265-17268;
Angew. Chem. 2019, 131, 17425-17428.
M. Anker, M. P. Coles, Angew. Chem. Int. Ed. 2019, 58, 18261-18265;
Angew. Chem. 2019, 131, 18429-18433.
D. Wendel, A. Porzelt, F. A. D. Herz, D. Sarkar, C. Jandl, S. Inoue, B. Rieger, J. Am. Chem. Soc. 2017, 139, 8134-8137;
R. Lalrempuia, A. Stasch, C. Jones, Chem. Sci. 2013, 4, 4383-4388.
M. D. Anker, R. J. Schwamm, M. P. Coles, Chem. Commun. 2020, 56, 2288-2291.