Formation and Cycloaddition Reactions of a Reactive Boraalkene Stabilized Internally by N-Heterocyclic Carbene.
boraalkenes
carbon dioxide
cycloaddition
diazoalkanes
nitrogen oxides
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:
01 Sep 2021
01 Sep 2021
Historique:
revised:
28
06
2021
received:
19
05
2021
pubmed:
6
7
2021
medline:
6
7
2021
entrez:
5
7
2021
Statut:
ppublish
Résumé
The synthesis of element-carbon double bonds is of great importance for the development and understanding of reactive π-bonded systems in chemistry. The seven-membered heterocyclic system 4 b is readily made by internal C-H activation at a pendent isopropyl methyl group of the respective [(IPr)C
Identifiants
pubmed: 34219331
doi: 10.1002/anie.202106724
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
19905-19911Subventions
Organisme : Alexander von Humboldt-Stiftung
Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
For reviews, see:
H. F. Schaefer, Acc. Chem. Res. 1982, 15, 283-290;
P. Metzner, Top. Curr. Chem. 1999, 204, 127-181.
See for examples:
M. W. Rathke, R. Kow, J. Am. Chem. Soc. 1972, 94, 6854-6856;
R. Kow, M. W. Rathke, J. Am. Chem. Soc. 1973, 95, 2715-2716;
M. M. Olmstead, P. P. Power, K. J. Weese, J. Am. Chem. Soc. 1987, 109, 2541-2542;
C.-W. Chiu, F. P. Gabbaï, Angew. Chem. Int. Ed. 2007, 46, 6878-6881;
Angew. Chem. 2007, 119, 7002-7005;
K. Watanabe, A. Ueno, X. Tao, K. Škoch, X. Jie, S. Vagin, B. Rieger, C. G. Daniliuc, M. Letzel, G. Kehr, G. Erker, Chem. Sci. 2020, 11, 7349-7355;
N. A. Phillips, R. Y. Kong, A. J. P. White, M. R. Crimmin, Angew. Chem. Int. Ed. 2021, 60, 12013-12019;
Angew. Chem. 2021, 133, 12120-12126.
See for example: T. A. Bartholome, A. Kaur, D. J. D. Wilson, J. L. Dutton, C. D. Martin, Angew. Chem. Int. Ed. 2020, 59, 11470-11476;
Angew. Chem. 2020, 132, 11567-11573.
For a review, see: P. G. Campbell, A. J. V. Marwitz, S.-Y. Liu, Angew. Chem. Int. Ed. 2012, 51, 6074-6092;
Angew. Chem. 2012, 124, 6178-6197.
For reviews, see:
A. Berndt, Angew. Chem. Int. Ed. Engl. 1993, 32, 985-1009;
Angew. Chem. 1993, 105, 1034-1058;
P. P. Power, Chem. Rev. 1999, 99, 3463-3503;
R. C. Fischer, P. P. Power, Chem. Rev. 2010, 110, 3877-3923;
R. Borthakur, V. Chandrasekhar, Coord. Chem. Rev. 2021, 429, 213647;
M. Devillard, G. Alcaraz in PATAI′S Chemistry of Functional Groups (Ed.: Z. Rappoport), Wiley-VCH, Weinheim, 2021,
https://doi.org/10.1002/9780470682531.pat0972.
For reviews, see:
A. B. Cuenca, E. Fernández, Chem. Soc. Rev. 2021, 50, 72-86;
R. J. Maza, J. J. Carbó, E. Fernández, Adv. Synth. Catal. 2021, 363, 2274-2289; see for examples:
B. Glaser, H. Nöth, Chem. Ber. 1986, 119, 3856-3858;
T. Tomioka, Y. Takahashi, T. G. Vaughan, T. Yanase, Org. Lett. 2010, 12, 2171-2173;
T. Wang, S. Kohrt, C. G. Daniliuc, G. Kehr, G. Erker, Org. Biomol. Chem. 2017, 15, 6223-6232.
See for examples:
H. Klusik, A. Berndt, Angew. Chem. Int. Ed. Engl. 1983, 22, 877-878;
Angew. Chem. 1983, 95, 895-896;
M. Pilz, J. Allwohn, R. Hunold, W. Massa, A. Berndt, Angew. Chem. Int. Ed. Engl. 1988, 27, 1370-1372;
Angew. Chem. 1988, 100, 1421-1422;
M. Pilz, J. Allwohn, P. Willershausen, W. Massa, A. Berndt, Angew. Chem. Int. Ed. Engl. 1990, 29, 1030-1032;
Angew. Chem. 1990, 102, 1085-1087.
See for examples:
B. Glaser, H. Nöth, Angew. Chem. Int. Ed. Engl. 1985, 24, 416-417;
Angew. Chem. 1985, 97, 424-425;
S. Helm, H. Nöth, Angew. Chem. Int. Ed. Engl. 1988, 27, 1331-1337;
Angew. Chem. 1988, 100, 1378-1384.
See for examples:
R. Boese, P. Paetzold, A. Tapper, Chem. Ber. 1987, 120, 1069-1071;
A. Tapper, T. Schmitz, P. Paetzold, Chem. Ber. 1989, 122, 595-601;
G. Gabbert, W. Weinmann, H. Pritzkow, W. Siebert, Angew. Chem. Int. Ed. Engl. 1992, 31, 1603-1605;
Angew. Chem. 1992, 104, 1670-1672.
R. Boese, P. Paetzold, A. Tapper, R. Ziembinski, Chem. Ber. 1989, 122, 1057-1060.
J. Böhnke, H. Braunschweig, T. Dellermann, W. C. Ewing, T. Kramer, I. Krummenacher, A. Vargas, Angew. Chem. Int. Ed. 2015, 54, 4469-4473;
Angew. Chem. 2015, 127, 4551-4555;
J. Böhnke, H. Braunschweig, T. Dellermann, W. C. Ewing, K. Hammond, J. O. C. Jimenez-Halla, T. Kramer, J. Mies, Angew. Chem. Int. Ed. 2015, 54, 13801-13805;
Angew. Chem. 2015, 127, 14006-14010.
L. Kong, W. Lu, Y. Li, R. Ganguly, R. Kinjo, Angew. Chem. Int. Ed. 2016, 55, 14718-14722;
Angew. Chem. 2016, 128, 14938-14942; see also:
B. Su, Y. Li, R. Ganguly, J. Lim, R. Kinjo, J. Am. Chem. Soc. 2015, 137, 11274-11277.
C. Chen, J. Li, C. G. Daniliuc, C. Mück-Lichtenfeld, G. Kehr, G. Erker, Angew. Chem. Int. Ed. 2020, 59, 21460-21464;
Angew. Chem. 2020, 132, 21644-21648; see also:
T. S. De Vries, A. Prokofjevs, E. Vedejs, Chem. Rev. 2012, 112, 4246-4282.
For review, see:
S. A. Iqbal, J. Pahl, K. Yuan, M. J. Ingleson, Chem. Soc. Rev. 2020, 49, 4564-4591, and references therein; see for an example:
J. M. Farrell, D. W. Stephan, Angew. Chem. Int. Ed. 2015, 54, 5214-5217;
Angew. Chem. 2015, 127, 5303-5306; For an intermolecular C−H bororation, see:
Y. Liu, W. Dong, Z.-H. Li, H. Wang, Chem 2021, 7, 1843-1851.
For reviews, see:
Y. Wang, G. H. Robinson, Inorg. Chem. 2014, 53, 11815-11832;
V. Nesterov, D. Reiter, P. Bag, P. Frisch, R. Holzner, A. Porzelt, S. Inoue, Chem. Rev. 2018, 118, 9678-9842; see for an example:
H. Braunschweig, R. D. Dewhurst, K. Hammond, J. Mies, K. Radacki, A. Vargas, Science 2012, 336, 1420-1422.
H. E. Winberg, J. Org. Chem. 1959, 24, 264-265;
F. R. Jensen, L. A. Smith, J. Am. Chem. Soc. 1964, 86, 956-957;
M. L. H. Green, D. K. P. Ng, Chem. Rev. 1995, 95, 439-473.
For comparison, see:
M. M. Morgan, J. M. Rautiainen, W. E. Piers, H. M. Tuononen, C. Gendy, Dalton Trans. 2018, 47, 734-741; see the reaction of boron-boron (multiple-)bond with CO2 for comparison:
A. Stoy, J. Böhnke, J. O. C. Jiménez-Halla, R. D. Dewhurst, T. Thiess, H. Braunschweig, Angew. Chem. Int. Ed. 2018, 57, 5947-5951;
Angew. Chem. 2018, 130, 6055-6059;
T. Trageser, D. Bebej, M. Bolte, H. Lerner, M. Wagner, Angew. Chem. Int. Ed. 2021, 60, 13500-13506;
Angew. Chem. 2021, 133, 13612-13618; For a Li+-induced [2+2] cycloaddition of B=S double bond with CO2, see:
C. Chen, C. G. Daniliuc, C. Mück-Lichtenfeld, G. Kehr, G. Erker, J. Am. Chem. Soc. 2020, 142, 19763-19771.
See for comparison: P. Paetzold, U. Englert, R. Finger, T. Schmitz, A. Tapper, R. Ziembinski, Z. Anorg. Allg. Chem. 2004, 630, 508-518.
See the reaction of diborene with chalcogens for comparison: H. Braunschweig, P. Constantinidis, T. Dellermann, W. C. Ewing, I. Fischer, M. Hess, F. R. Knight, A. Rempel, C. Schneider, S. Ullrich, A. Vargas, J. D. Woollins, Angew. Chem. Int. Ed. 2016, 55, 5606-5609;
Angew. Chem. 2016, 128, 5697-5700.
For reviews, see:
R. Huisgen, Angew. Chem. Int. Ed. Engl. 1963, 2, 565-598;
Angew. Chem. 1963, 75, 604-637;
M. Breugst, H.-U. Reissig, Angew. Chem. Int. Ed. 2020, 59, 12293-12307;
Angew. Chem. 2020, 132, 12389-12404.
K. Severin, Chem. Soc. Rev. 2015, 44, 6375-6386; see for a comparison:
P. W. Antoni, C. Golz, J. J. Holstein, D. A. Pantanzis, M. M. Hansmann, Nat. Chem. 2021, 13, 587-593.
See for comparison:
A. J. P. Cardenas, B. J. Culotta, T. H. Warren, S. Grimme, A. Stute, R. Fröhlich, G. Kehr, G. Erker, Angew. Chem. Int. Ed. 2011, 50, 7567-7571;
Angew. Chem. 2011, 123, 7709-7713;
D. Beaudoin, J. D. Wuest, Chem. Rev. 2016, 116, 258-286.
Deposition Numbers 2059122 (for 4b), 2059123 (for 5a), 2059124 (for 5b), 2059125 (for 6b), 2059126 (for 8), 2059127 (for 9a), 2091486 (for 9b), 2091487 (for 9c), 2059128 (for 10), 2059129 (for 11), 2059134 (for 12), 2059135 (for 13), 2059137 (for 14eq), 2059136 (14ax), 2062438 (for 15eq), 2059138 (for 15ax), 2059139 (for 16), 2059140 (for 18) and 2059141 (for 19) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service www.ccdc.cam.ac.uk/structures.