Structural and Synthetic Insights on Oxidative Homocouplings of Alkynes Mediated by Alkali-Metal Manganates.
1,3-diynes
alkali-metal effect
homocoupling
manganates
metal - metal cooperativity
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
13 Jun 2023
13 Jun 2023
Historique:
received:
22
02
2023
medline:
18
3
2023
pubmed:
18
3
2023
entrez:
17
3
2023
Statut:
ppublish
Résumé
Exploiting bimetallic cooperation alkali-metal manganate (II) complexes can efficiently promote oxidative homocoupling of terminal alkynes furnishing an array of conjugated 1,3-diynes. The influence of the alkali-metal on these C-C bond forming processes has been studied by preparing and structurally characterizing the alkali-metal tetra(alkyl) manganates [(TMEDA)
Identifiants
pubmed: 36929782
doi: 10.1002/chem.202300593
doi:
Substances chimiques
Alkynes
0
phenylacetylene
239WSR2IBO
Sodium
9NEZ333N27
Lithium
9FN79X2M3F
Alkalies
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300593Subventions
Organisme : Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
ID : 206021_177033
Organisme : Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
ID : 188573
Organisme : Royal Society
ID : URF\R1\221304
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
A. L. L. Shi Shun, R. R. Tykwinski, Angew. Chem. Int. Ed. 2006, 45, 1034-1057.
W. Shi, Curr. Organocatal. 2015, 2, 2-13.
J. Liu, J. W. Y. Lam, B. Z. Tang, Chem. Rev. 2009, 109, 5799-5867;
J. M. Tour, Chem. Rev. 1996, 96, 537-554;
K. S. Sindhu, G. Anilkumar, RSC Adv. 2014, 4, 27867-27887;
P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. Int. Ed. 2000, 39, 2565-2786.
R. Kinjo, B. Donnadieu, G. Bertrand, Angew. Chem. Int. Ed. 2011, 50, 5403-5585;
L. Wang, X. Yu, X. Feng, M. Bao, J. Org. Chem. 2013, 78, 1693-1698;
S. M. Weber, G. Hilt, Org. Lett. 2019, 21, 4106-4110;
S. Kramer, J. L. H. Madsen, M. Rottländer, T. Skrydstrup, Org. Lett. 2010, 12, 2758-2761;
L. Wang, X. Yu, X. Feng, M. Bao, Org. Lett. 2012, 14, 2418-2421.
C. Glaser, Ber. Dtsch. Chem. Ges. 1869, 2, 422-424;
C. Glaser, Ann. Chem. Pharm. 1870, 154, 137-171.
A. Hay, J. Org. Chem. 1960, 25, 1275-1276;
A. Hay, J. Org. Chem. 1962, 27, 3320-3321.
K. Kamata, S. Yamaguchi, M. Kotani, K. Yamaguchi, N. Mizuno, Angew. Chem. Int. Ed. 2008, 47, 2407-2410;
T. Oishi, T. Katayama, K. Yamaguchi, N. Mizuno, Chem. Eur. J. 2009, 15, 7539-7542;
H.-F. Jiang, J.-Y. Tang, A.-Z. Wang, G.-H. Deng, S.-R. Yang, Synthesis 2006, 1155-1161;
G. Eglinton, A. R. Galbraith, J. Chem. Soc. 1959, 889-896;
J. S. Yadav, B. V. S. Reddy, K. B. Reddy, K. U. Gayathri, A. R. Prasad, Tet. Lett. 2003, 44, 6493-6496.
G. Hilt, C. Hengst, M. Arndt, Synthesis 2009, 395-398.
J.-F. Han, P. Guo, L. Chen, K.-Y. Ye, Synthesis 2022, 54, 1989-1995.
G. Cahiez, A. Moyeux, J. Buendia, C. Duplais, J. Am. Chem. Soc. 2007, 129, 13788-13789.
Y. Liu, J. Berges, Y. Zaid, F. O. Chahdi, A. Van Der Lee, D. Harakat, E. Clot, F. Jaroschik, M. Taillefer, J. Org. Chem. 2019, 84, 4413-4420.
M. Uzelac, P. Mastropierro, M. de Tullio, I. Borilovic, M. Tarres, A. R. Kennedy, G. Aromi, E. Hevia, Angew. Chem. Int. Ed. 2021, 60, 3247-3253.
R. E. Mulvey, F. Mongin, M. Uchiyama, Y. Kondo, Angew. Chem. Int. Ed. 2007, 46, 3802-3824;
T. Klatt, J. T. Markiewciz, C. Saemann, P. Knochel, J. Org. Chem. 2014, 79, 4253-4269;
A. Harrison-Marchand, F. Mongin, Chem. Rev. 2013, 113, 7470-7562;
A. Harrison-Marchand, F. Mongin, Chem. Rev. 2013, 113, 7563-7727;
S. D. Robertson, M. Uzelac, R. E. Mulvey, Chem. Rev. 2019, 119, 8332-8405.
S. E. Baillie, T. D. Bluemke, W. Clegg, A. R. Kennedy, J. Klett, L. Russo, M. de Tullio, E. Hevia, Chem. Commun. 2014, 50, 12859-12862.
L. Davin, A. Hernan-Gomez, C. McLaughlin, A. R. Kennedy, R. McLellan, E. Hevia, Dalton Trans. 2019, 48, 8122-8130.
M. Fairley, L. Davin, A. Hernan-Gomez, J. Garcia-Alvarez, C. T. O'Hara, E. Hevia, Chem. Sci. 2019, 10, 5821-5831.
J. M. Gil-Negrete, E. Hevia, Chem. Sci. 2021, 12, 1982-1992.
A. J. Hart, D. H. O'Brien, C. R. Russell, J. Organomet. Chem. 1974, 72, C19-C22;
B. Conway, D. V. Graham, E. Hevia, A. R. Kennedy, J. Klett, R. E. Mulvey, Chem. Commun. 2008, 2638-2640;
W. Clegg, B. Conway, A. R. Kennedy, J. Klett, R. E. Mulvey, L. Russo, Eur. J. Inorg. Chem. 2011, 721-726.
R. A. Andersen, E. Carmona-Guzman, J. F. Gibson, G. Wilkinson, J. Chem. Soc. Dalton Trans. 1976, 2204-2211.
D. E. Anderson, A. Tortajada, E. Hevia, Angew. Chem. Int. Ed. 2023, 62, e202218498.
L. M. Carrella, W. Clegg, D. V. Graham, L. M. Hogg, A. R. Kennedy, J. Klett, R. E. Mulvey, E. Rentschler, L. Russo, Angew. Chem. Int. Ed. 2007, 46, 4662-4666.
M. Uzelac, I. Borilovic, M. Amores, T. Cadenbach, A. R. Kennedy, G. Aromi, E. Hevia, Chem. Eur. J. 2016, 22, 4843-4854.
L. C. H. Maddock, T. Nixon, A. R. Kennedy, M. R. Probert, W. Clegg, E. Hevia, Angew. Chem. Int. Ed. 2018, 57, 187-191;
L. C. H. Maddock, M. Mu, A. R. Kennedy, M. Garcia-Melchor, E. Hevia, Angew. Chem. Int. Ed. 2021, 60, 15296-15301.
A. Logallo, M. Mu, M. Garcia-Melchor, E. Hevia, Angew. Chem. Int. Ed. 2022, 61, e202213246.
A. Bottoni, G. Cahiez, M. Calvaresi, A. Moyeux, P. Giacinto, G. P. Miscione, J. Organomet. Chem. 2016, 814, 25-34.
A. Alberola, V. L. Blair, L. M. Carrella, W. Clegg, A. R. Kennedy, J. Klett, R. E. Mulvey, S. Newton, E. Rentschler, L. Russo, Organometallics 2009, 28, 2112-2118.
S. Kheradmandan, T. Fox, H. W. Schmalle, K. Venkatesan, H. Berke, Eur. J. Inorg. Chem. 2004, 3544-3554.
G. M. Yee, K. Kowolik, S. Manabe, J. C. Fettinger, L. A. Berben, Chem. Commun. 2011, 47, 11680-11682.
C. Soria Alvarez, S. R. Boss, J. C. Burley, S. M. Humphry, R. A. Layfield, R. A. Kowenicki, M. McPartlin, J. M. Rawson, A. E. H. Wheatley, P. T. Wood, D. S. Wright, Dalton Trans. 2004, 3481-3487;
C. Ni, J. C. Fettinger, G. J. Long, P. P. Power, Dalton Trans. 2010, 39, 10664-10670;
U. Chakraborty, S. Demeshko, F. Meyer, A. J. von Wangelin, Angew. Chem. Int. Ed. 2019, 58, 3466-3470.
M. de Tullio, A. M. Borys, A. Hernan-Gomez, A. R. Kennedy, E. Hevia, Chem. Catalysis 2021, 1, 1308-1321.
V. V. Ktivykh, I. L. Eremenko, D. Veghini, I. A. Petrunenko, D. L. Poutney, D. Unseld, H. Berke, J. Organomet. Chem. 1996, 511, 111-114.
F. J. Fernandez, M. Alfonso, H. W. Schmalle, H. Berke, Organometallics 2001, 20, 3122-3131.
CrysAlisPro, Agil. Technol. Version 1.1 71.35.19 (release 27-10-2011 CrysAlis171.NET) (compiled Oct 27 2011,150211).
L. J. Farrugia, J. Appl. Crystallogr. 2012, 45, 849-854.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Crystallogr. 2009, 42, 339-341.
G. M. Sheldrick, Acta Crystallogr. Sect. A 2015, 71, 3-8.
G. M. Sheldrick, Acta Crystallogr. Sect. C 2015, 71, 3-8.
L. Palatinus, A. Van der Lee, J. Appl. Crystallogr. 2008, 41, 975-984;
L. Palatinus, S. J. Prathapa, S. Van Smaalen, J. Appl. Crystallogr. 2012, 45, 575-580;
G. M. Sheldrick, Acta Crystallogr. 2008, A64, 112-122.