Iridium-Catalyzed C(sp
Borylation
C(sp3)−H Functionalization
Iridium Catalysis
Ligand Design
Pincer Complex
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:
23 May 2022
23 May 2022
Historique:
received:
11
02
2022
pubmed:
10
3
2022
medline:
10
3
2022
entrez:
9
3
2022
Statut:
ppublish
Résumé
New ligands for the iridium-catalyzed C(sp
Identifiants
pubmed: 35262270
doi: 10.1002/anie.202202327
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202202327Subventions
Organisme : Japan Society for the Promotion of Science
ID : JP 20H04824
Organisme : Japan Society for the Promotion of Science
ID : JP 21H01941
Organisme : Japan Society for the Promotion of Science
ID : JP 21K14628
Organisme : Yamada Science Fundation
Informations de copyright
© 2022 Wiley-VCH GmbH.
Références
M. C. White, Science 2012, 335, 807-809;
J. F. Hartwig, J. Am. Chem. Soc. 2016, 138, 2-24;
J. F. Hartwig, M. A. Larsen, ACS Cent. Sci. 2016, 2, 281-292;
K. I. Goldberg, A. S. Goldman, Acc. Chem. Res. 2017, 50, 620-626;
A. Kumar, T. M. Bhatti, A. S. Goldman, Chem. Rev. 2017, 117, 12357-12384;
M. C. White, J. Zhao, J. Am. Chem. Soc. 2018, 140, 13988-14009;
L. Capaldo, D. Ravelli, M. Fagnoni, Chem. Rev. 2022, 122, 1875-1924.
M. S. Chen, M. C. White, Science 2007, 318, 783-787;
M. S. Chen, M. C. White, Science 2010, 327, 566-571;
P. E. Gormisky, M. C. White, J. Am. Chem. Soc. 2013, 135, 14052-14055;
J. M. Howell, K. Feng, J. R. Clark, L. J. Trzepkowski, M. C. White, J. Am. Chem. Soc. 2015, 137, 14590-14593;
T. J. Osberger, D. C. Rogness, J. T. Kohrt, A. F. Stepan, M. C. White, Nature 2016, 537, 214-219;
T. Nanjo, E. C. de Lucca, M. C. White, J. Am. Chem. Soc. 2017, 139, 14586-14591;
J. R. Clark, K. Feng, A. Sookezian, M. C. White, Nat. Chem. 2018, 10, 583-591;
J. Zhao, T. Nanjo, E. C. de Lucca, M. C. White, Nat. Chem. 2019, 11, 213-221;
K. Feng, R. E. Quevedo, J. T. Kohrt, M. S. Oderinde, U. Reilly, M. C. White, Nature 2020, 580, 621-627.
K. Liao, S. Negretti, D. G. Musaev, J. Bacsa, H. M. L. Davies, Nature 2016, 533, 230-234;
K. Liao, T. C. Pickel, V. Boyarskikh, J. Bacsa, D. G. Musaev, H. M. L. Davies, Nature 2017, 551, 609-613.
R. R. Karimov, A. Sharma, J. F. Hartwig, ACS Cent. Sci. 2016, 2, 715-724;
A. Bunescu, S. Lee, Q. Li, J. F. Hartwig, ACS Cent. Sci. 2017, 3, 895-903;
L. Chen, K. G. Malollari, A. Uliana, J. F. Hartwig, J. Am. Chem. Soc. 2021, 143, 4531-4535.
I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890-931;
L. Xu, G. Wang, S. Zhang, H. Wang, L. Wang, L. Liu, J. Jiao, P. Li, Tetrahedron 2017, 73, 7123-7157.
Functionalization of methane was also investigated. See:
A. K. Cook, S. D. Schimler, A. J. Matzger, M. S. Sanford, Science 2016, 351, 1421-1424;
K. T. Smith, S. Berritt, M. González-Moreiras, S. Ahn, M. R. Smith, M.-H. Baik, D. J. Mindiola, Science 2016, 351, 1424-1427.
C. W. Liskey, J. F. Hartwig, J. Am. Chem. Soc. 2012, 134, 12422-12425;
T. Ohmura, T. Torigoe, M. Suginome, J. Am. Chem. Soc. 2012, 134, 17416-17419;
C. W. Liskey, J. F. Hartwig, J. Am. Chem. Soc. 2013, 135, 3375-3378;
T. Ohmura, T. Torigoe, M. Suginome, Organometallics 2013, 32, 6170-6173;
T. Ohmura, T. Torigoe, M. Suginome, Chem. Commun. 2014, 50, 6333-6336;
Q. Li, C. W. Liskey, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136, 8755-8765;
T. Ohmura, I. Sasaki, T. Torigoe, M. Suginome, Organometallics 2016, 35, 1601-1603;
T. Torigoe, T. Ohmura, M. Suginome, J. Org. Chem. 2017, 82, 2943-2956.
Ir/Me4phen catalyst system first appeared in the intramolecular C(sp3)−H silylation. See: E. M. Simmons, J. F. Hartwig, Nature 2012, 483, 70-73.
2,9-Dimethyl-1,10-phenanthroline was shown as a suitable ligand for the iridium-catalyzed C(sp3)−H borylation of cyclopropane. See: ref [7c].
3,8-Diaryl-1,10-phenanthrolines were also investigated for the iridium-catalyzed C(sp3)−H borylation. See:
M. A. Larsen, C. V. Wilson, J. F. Hartwig, J. Am. Chem. Soc. 2015, 137, 8633-8643;
M. A. Larsen, R. J. Oeschger, J. F. Hartwig, ACS Catal. 2020, 10, 3415-3424.
R. Oeschger, B. Su, I. Yu, C. Ehinger, E. Romero, S. He, J. Hartwig, Science 2020, 368, 736-741.
M. R. Jones, C. D. Fast, N. D. Schley, J. Am. Chem. Soc. 2020, 142, 6488-6492.
M. Zhang, H. Wu, J. Yang, G. A. Huang, ACS Catal. 2021, 11, 4833-4847.
Preparation of a boryl-bipyridine ligand and its application for the iridium-catalyzed aromatic C(sp2)−H borylation has been reported. See: S. Ding, L. Wang, Z. Miao, P. Li, Molecules 2019, 24, 1434.
Preparation of an amine-pyridine-silyl ligand and its application for the iridium-catalyzed H-D exchange between Si−H and aromatic C(sp2)−D has been reported. See: T. Komuro, T. Osawa, R. Suzuki, D. Mochizuki, H. Higashi, H. Tobita, Chem. Commun. 2019, 55, 957-960.
Conjugated pyridine-based benzylsilanes are relatively unstable. In terms of stability, we chose t-Bu group as substituents on the silicon.
R.-L. Zhong, S. Sakaki, J. Am. Chem. Soc. 2019, 141, 9854-9866.
To obtain satisfactory results in the Ir/L3-catalyzed borylation, use of 60 equiv of 1 a was required. See Supporting Information for details.