Carbocationoids, a concept for controlling highly reactive cationic species.
Journal
Communications chemistry
ISSN: 2399-3669
Titre abrégé: Commun Chem
Pays: England
ID NLM: 101725670
Informations de publication
Date de publication:
13 Mar 2024
13 Mar 2024
Historique:
received:
15
02
2024
accepted:
01
03
2024
medline:
14
3
2024
pubmed:
14
3
2024
entrez:
14
3
2024
Statut:
epublish
Résumé
Carbocations, which are positively charged highly electrophilic intermediates, are efficacious for the direct alkylation of low-reactive nucleophiles. The utilization of carbocations in S
Identifiants
pubmed: 38480821
doi: 10.1038/s42004-024-01139-w
pii: 10.1038/s42004-024-01139-w
doi:
Types de publication
Journal Article
Langues
eng
Pagination
55Subventions
Organisme : MEXT | Japan Society for the Promotion of Science (JSPS)
ID : 21H02603
Organisme : MEXT | Japan Society for the Promotion of Science (JSPS)
ID : 17H03970
Organisme : MEXT | Japan Society for the Promotion of Science (JSPS)
ID : 26670001
Informations de copyright
© 2024. The Author(s).
Références
Olah, G. A. 100 years of carbocations and their significance in chemistry. J. Org. Chem. 66, 5943–5957 (2001).
doi: 10.1021/jo010438x
pubmed: 11529717
Aue, D. H. Carbocations. Wiley Interdiscip. Rev. Comput. Mol. Sci. 1, 487–508 (2011).
doi: 10.1002/wcms.12
Dryzhakov, M., Richmond, E. & Moran, J. Recent advances in direct catalytic dehydrative substitution of alcohols. Synthesis 48, 935–959 (2016).
doi: 10.1055/s-0035-1560396
Baeza, A. & Nájera, C. Recent advances in the direct nucleophilic substitution of allylic alcohols through S
doi: 10.1055/s-0033-1340316
Chen, L., Yin, X. P., Wang, C. H. & Zhou, J. Catalytic functionalization of tertiary alcohols to fully substituted carbon centres. Org. Biomol. Chem. 12, 6033–6048 (2014).
doi: 10.1039/C4OB00718B
pubmed: 24915514
Emer, E. et al. Direct nucleophilic S
doi: 10.1002/ejoc.201001474
Nishimoto, Y., Saito, T., Yasuda, M. & Baba, A. Indium-catalyzed coupling reaction between silyl enolates and alkyl chlorides or alkyl ethers. Tetrahedron 65, 5462–5471 (2009).
doi: 10.1016/j.tet.2009.03.106
Reetz, M. T. Lewis acid induced α-alkylation of carbonyl compounds. Angew. Chem. Int. Ed.Angew. Chem. Int. Ed. 21, 96–108 (1982).
doi: 10.1002/anie.198200961
Naredla, R. R. & Klumpp, D. A. Contemporary carbocation chemistry: applications in organic synthesis. Chem. Rev. 113, 6905–6948 (2013).
doi: 10.1021/cr4001385
pubmed: 23819438
Zhu, Q., Gentry, E. C. & Knowles, R. R. Catalytic carbocation generation enabled by the mesolytic cleavage of alkoxyamine radical cations. Angew. Chem. Int. Ed. 55, 9969–9973 (2016).
doi: 10.1002/anie.201604619
Ammer, J. & Mayr, H. Photogeneration of carbocations: applications in physical organic chemistry and the design of suitable precursors. J. Phys. Org. Chem. 26, 956–969 (2013).
doi: 10.1002/poc.3132
Olah, G., Svoboda, J. & Olah, J. Preparative carbocation chemistry; IV. Improved preparation of triphenylcarbenium (trityl) salts. Synthesis 1972, 544 (2002).
doi: 10.1055/s-1972-21914
Bollinger, J. M., Comisarow, M. B., Cupas, C. A. & Olah, G. A. Stable carbonium ions. XLV. Benzyl cations. J. Am. Chem. Soc. 89, 5687–5691 (1967).
doi: 10.1021/ja00998a034
Cupas, C. A., Comisarow, M. B. & Olah, G. A. Stable carbonium ions. XIX. Benzyl Cations. J. Am. Chem. Soc. 88, 361–362 (1966).
doi: 10.1021/ja00954a034
Yoshida, J. I., Shimizu, A. & Hayashi, R. Electrogenerated cationic reactive intermediates: the pool method and further advances. Chem. Rev. 118, 4702–4730 (2018).
doi: 10.1021/acs.chemrev.7b00475
pubmed: 29077393
Yoshida, J. & Suga, S. Basic concepts of “Cation Pool” and “Cation Flow” methods and their applications in conventional and combinatorial organic synthesis. Chem. Eur. J. 8, 2650–2658 (2002).
doi: 10.1002/1521-3765(20020617)8:12<2650::AID-CHEM2650>3.0.CO;2-S
Caballero, A. & Pérez, P. J. Dimensioning the term carbenoid. Chem. Eur. J. 23, 14389–14393 (2017).
doi: 10.1002/chem.201702392
pubmed: 28640943
Fujita, H., Hayakawa, N. & Kunishima, M. Study of the reactivities of acid-catalyzed O-benzylating reagents based on structural isomers of 1,3,5-triazine. J. Org. Chem. 80, 11200–11205 (2015).
doi: 10.1021/acs.joc.5b02059
pubmed: 26458142
Lemieux, R. U. & Kondo, T. Benzyl trifluoromethanesulfonate. Preparation of tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl bromide from 1,3,4,6-tetra-O-acetyl-α-D-galactopyranose. Carbohydr. Res. 35, C4–C6 (1974).
doi: 10.1016/S0008-6215(00)84859-4
Fujita, H., Kakuyama, S. & Kunishima, M. N,N'-dimethylated benzyloxytriazinedione: a stable solid reagent for acid-catalyzed O-benzylation. Eur. J. Org. Chem. 833–839 (2017).
Fujita, H. et al. Preparation of alkyl ethers with diallyltriazinedione-type alkylating agents (ATTACKs-R) under acid catalysis. Eur. J. Org. Chem. 4436–4446 (2019).
Fujita, H., Terasaki, H., Kakuyama, S., Hioki, K. & Kunishima, M. Development of a storable triazinone-based reagent for O-p-methoxybenzylation under mild heating conditions. Org. Lett. 21, 3093–3097 (2019).
doi: 10.1021/acs.orglett.9b00732
pubmed: 31008611
Yamada, K., Fujita, H., Kitamura, M. & Kunishima, M. A practical method for p-methoxybenzylation of hydroxy groups using 2,4,6-tris(p-methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM). Synthesis 45, 2989–2997 (2013).
doi: 10.1055/s-0033-1339713
Yamada, K., Fujita, H. & Kunishima, M. A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure. Org. Lett. 14, 5026–5029 (2012).
doi: 10.1021/ol302222p
pubmed: 22994426
Nishimoto, Y., Onishi, Y., Yasuda, M. & Baba, A. α‐Alkylation of carbonyl compounds by direct addition of alcohols to enol acetates. Angew. Chem. Int. Ed. 48, 9131–9134 (2009).
doi: 10.1002/anie.200904069
Yasuda, M., Saito, T., Ueba, M. & Baba, A. Direct substitution of the hydroxy group in alcohols with silyl nucleophiles catalyzed by indium trichloride. Angew. Chem. Int. Ed. 43, 1414–1416 (2004).
doi: 10.1002/anie.200353121
Estopiñá-Durán, S., Mclean, E. B., Donnelly, L. J., Hockin, B. M. & Taylor, J. E. Arylboronic acid catalyzed C-alkylation and allylation reactions using benzylic alcohols. Org. Lett. 22, 7547–7551 (2020).
doi: 10.1021/acs.orglett.0c02736
pubmed: 32959662
pmcid: 8155392
Yamada, K., Karuo, Y., Tsukada, Y. & Kunishima, M. Mild amide-cleavage reaction mediated by electrophilic benzylation. Chem. Eur. J. 22, 14042–14047 (2016).
doi: 10.1002/chem.201603120
pubmed: 27529837
Estopiñá‐Durán, S. et al. Aryl boronic acid catalysed dehydrative substitution of benzylic alcohols for C−O bond formation. Chem. Eur. J. 25, 3950–3956 (2019).
doi: 10.1002/chem.201806057
pubmed: 30629761
Lu, K. et al. Monoalkylation of aniline with trichloroacetimidate catalyzed by (±)-camphorsulfonic acid through an S
doi: 10.1039/D0NJ00239A
Wallach, D. R., Stege, P. C., Shah, J. P. & Chisholm, J. D. Brønsted acid catalyzed monoalkylation of anilines with trichloroacetimidates. J. Org. Chem. 80, 1993–2000 (2015).
doi: 10.1021/jo5027222
pubmed: 25568933
Yokoyama, Y. et al. Samarium(II) dibromide-promoted selective deprotection of a benzoyl protective group. Synth. Commun. 48, 1025–1032 (2018).
doi: 10.1080/00397911.2018.1429634