McDonald, R. I., Liu, G. & Stahl, S. S. Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications. Chem. Rev. 111, 2981–3019 (2011).
Article CAS PubMed PubMed Central Google Scholar
Mann, S. E., Benhamou, L. & Sheppard, T. D. Palladium(II)-catalysed oxidation of alkenes. Synthesis 47, 3079–3117 (2015).
Hemric, B. M. Beyond osmium: progress in 1,2-amino oxygenation of alkenes, 1,3-dienes, alkynes, and allenes. Org. Biomol. Chem. 19, 46–81 (2021).
Article CAS PubMed Google Scholar
He, J., Wasa, M., Chan, K. S. L., Shao, Q. & Yu, J.-Q. Palladium-catalyzed transformations of alkyl C–H bonds. Chem. Rev. 117, 8754–8786 (2017).
Article CAS PubMed Google Scholar
Voica, A.-F., Mendoza, A., Gutekunst, W. R., Fraga, J. O. & Baran, P. S. Guided desaturation of unactivated aliphatics. Nat. Chem. 4, 629–635 (2012).
Article CAS PubMed PubMed Central Google Scholar
Chu, J. C. K. & Rovis, T. Amide-directed photoredox-catalysed C–C bond formation at unactivated sp3 C–H bonds. Nature 539, 272–275 (2016).
Article PubMed PubMed Central Google Scholar
Choi, G. J., Zhu, Q., Miller, D. C., Gu, C. J. & Knowles, R. R. Catalytic alkylation of remote C–H bonds enabled by proton-coupled electron transfer. Nature 539, 268–271 (2016).
Article CAS PubMed PubMed Central Google Scholar
Chan, H. S. S., Yang, J.-M. & Yu, J.-Q. Catalyst-controlled site-selective methylene C–H lactonization of dicarboxylic acids. Science 376, 1481–1487 (2022).
Article CAS PubMed Google Scholar
Vasseur, A., Bruffaerts, J. & Marek, I. Remote functionalization through alkene isomerization. Nat. Chem. 8, 209–219 (2016).
Article CAS PubMed Google Scholar
Janssen-Müller, D., Sahoo, B., Sun, S.-Z. & Martin, R. Tackling remote sp3 C–H functionalization via Ni-catalyzed ‘chain-walking’ reactions. Isr. J. Chem. 60, 195–206 (2020).
Dhungana, R. K., Sapkota, R. R., Niroula, D. & Giri, R. Walking metals: catalytic difunctionalization of alkenes at nonclassical sites. Chem. Sci. 11, 9757–9774 (2020).
Article CAS PubMed PubMed Central Google Scholar
Li, Y., Wu, D., Cheng, H.-G. & Yin, G. Difunctionalization of alkenes involving metal migration. Angew. Chem. Int. Ed. 59, 7990–8003 (2020).
Fiorito, D., Scaringi, S. & Mazet, C. Transition metal-catalyzed alkene isomerization as an enabling technology in tandem, sequential and domino processes. Chem. Soc. Rev. 50, 1391–1406 (2021).
Article CAS PubMed Google Scholar
Bonfield, H. E., Valette, D., Lindsay, D. M. & Reid, M. Stereoselective remote functionalization via palladium-catalyzed redox-relay Heck methodologies. Chem. Eur. J. 27, 158–174 (2021).
Article CAS PubMed Google Scholar
Massad, I., Suresh, R., Segura, L. & Marek, I. Stereoselective synthesis through remote functionalization. Nat. Synth. 1, 37–48 (2022).
Seayad, A. et al. Internal olefins to linear amines. Science 297, 1676–1678 (2002).
Article CAS PubMed Google Scholar
Obligacion, J. V. & Chirik, P. J. Bis(imino)pyridine cobalt-catalyzed alkene isomerization-hydroboration: a strategy for remote hydrofunctionalization with terminal selectivity. J. Am. Chem. Soc. 135, 19107–19110 (2013).
Article CAS PubMed Google Scholar
Atienza, C. C. H. et al. Bis(imino)pyridine cobalt-catalyzed dehydrogenative silylation of alkenes: scope, mechanism, and origins of selective allylsilane formation. J. Am. Chem. Soc. 136, 12108–12118 (2014).
Article CAS PubMed Google Scholar
Buslov, I., Becouse, J., Mazza, S., Montandon-Clerc, M. & Hu, X. L. Chemoselective alkene hydrosilylation catalyzed by nickel pincer complexes. Angew. Chem. Int. Ed. 54, 14523–14526 (2015).
Jia, X. & Huang, Z. Conversion of alkanes to linear alkylsilanes using an iridium–iron-catalysed tandem dehydrogenation–isomerization–hydrosilylation. Nat. Chem. 8, 157–161 (2016).
Article CAS PubMed Google Scholar
Dupuy, S., Zhang, K. F., Goutierre, A. S. & Baudoin, O. Terminal-selective functionalization of alkyl chains by regioconvergent cross-coupling. Angew. Chem. Int. Ed. 55, 14793–14797 (2016).
Juliá-Hernández, F., Moragas, T., Cornella, J. & Martin, R. Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide. Nature 545, 84–88 (2017).
Yang, J. et al. Direct synthesis of adipic acid esters via palladium-catalyzed carbonylation of 1,3-dienes. Science 366, 1514–1517 (2019).
Article CAS PubMed Google Scholar
Li, X., Jin, J., Chen, P. & Liu, G. Catalytic remote hydrohalogenation of internal alkenes. Nat. Chem. 14, 425–432 (2022).
Article CAS PubMed Google Scholar
Masarwa, A. et al. Merging allylic carbon–hydrogen and selective carbon–carbon bond activation. Nature 505, 199–203 (2014).
Article CAS PubMed Google Scholar
Hamasaki, T., Aoyama, Y., Kawasaki, J., Kakiuchi, F. & Kochi, T. Chain walking as a strategy for carbon–carbon bond formation at unreactive sites in organic synthesis: catalytic cycloisomerization of various 1,n-dienes. J. Am. Chem. Soc. 137, 16163–16171 (2015).
Article CAS PubMed Google Scholar
He, Y., Cai, Y. & Zhu, S. Mild and regioselective benzylic C–H functionalization: Ni-catalyzed reductive arylation of remote and proximal olefins. J. Am. Chem. Soc. 139, 1061–1064 (2017).
Article CAS PubMed Google Scholar
Kundu, G., Opincal, F., Sperger, T. & Schoenebeck, F. Air-stable PdI dimer enabled remote functionalization: access to fluorinated 1,1-diaryl alkanes with unprecedented speed. Angew. Chem. Int. Ed. 61, e202113667 (2022).
Xiao, J., He, Y., Ye, F. & Zhu, S. Remote sp3 C–H amination of alkenes with nitroarenes. Chem 4, 1645–1657 (2018).
Yu, X. et al. Site-selective alkene borylation enabled by synergistic hydrometallation and borometallation. Nat. Catal. 3, 585–592 (2020).
Lee, C., Seo, H., Jeon, J. & Hong, S. γ-Selective C(sp3)–H amination via controlled migratory hydroamination. Nat. Commun. 12, 5657–5665 (2021).
Article CAS PubMed PubMed Central Google Scholar
Werner, E. W., Mei, T.-S., Burckle, A. J. & Sigman, M. S. Enantioselective Heck arylations of acyclic alkenyl alcohols using a redox-relay strategy. Science 338, 1455–1458 (2012).
Article CAS PubMed PubMed Central Google Scholar
Mei, T.-S., Patel, H. H. & Sigman, M. S. Enantioselective construction of remote quaternary stereocentres. Nature 508, 340–344 (2014).
Article CAS PubMed PubMed Central Google Scholar
Singh, S., Bruffaerts, J., Vasseur, A. & Marek, I. A unique Pd-catalysed Heck arylation as a remote trigger for cyclopropane selective ring-opening. Nat. Commun. 8, 14200–14209 (2017).
Article PubMed PubMed Central Google Scholar
Kohler, D. G., Gockel, S. N., Kennemur, J. L., Waller, P. J. & Hull, K. L. Palladium-catalysed anti-Markovnikov selective oxidative amination. Nat. Chem. 10, 333–340 (2018).
Article CAS PubMed PubMed Central Google Scholar
Kou, X., Shao, Q., Ye, C., Yang, G. & Zhang, W. Asymmetric aza-Wacker-type cyclization of N-Ts hydrazine-tethered tetrasubstituted olefins: synthesis of pyrazolines bearing one quaternary or two vicinal stereocenters. J. Am. Chem. Soc. 140, 7587–7597 (2018).
Article CAS PubMed Google Scholar
Liu, J., Yuan, Q., Toste, F. D. & Sigman, M. S. Enantioselective construction of remote tertiary carbon–fluorine bonds. Nat. Chem. 11, 710–715 (2019).
Article CAS PubMed PubMed Central Google Scholar
Han, C. et al. Palladium-catalyzed remote 1,n-arylamination of unactivated terminal alkenes. ACS Catal. 9, 4196–4202 (2019).
留言 (0)