Multi-site programmable functionalization of alkenes via controllable alkene isomerization

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).

Article  CAS  Google Scholar 

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).

Article  Google Scholar 

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).

Article  CAS  Google Scholar 

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).

Article  Google Scholar 

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).

Article  CAS  Google Scholar 

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).

Article  CAS  Google Scholar 

Juliá-Hernández, F., Moragas, T., Cornella, J. & Martin, R. Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide. Nature 545, 84–88 (2017).

Article  PubMed  Google Scholar 

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).

Article  CAS  Google Scholar 

Xiao, J., He, Y., Ye, F. & Zhu, S. Remote sp3 C–H amination of alkenes with nitroarenes. Chem 4, 1645–1657 (2018).

Article  CAS  Google Scholar 

Yu, X. et al. Site-selective alkene borylation enabled by synergistic hydrometallation and borometallation. Nat. Catal. 3, 585–592 (2020).

Article  CAS  Google Scholar 

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).

Article  CAS 

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