Shire, B. R. & Anderson, E. A. Conquering the synthesis and functionalization of bicyclo[1.1.1]pentanes. JACS Au 3, 1539–1553 (2023).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Bellotti, P. & Glorius, F. Strain-release photocatalysis. J. Am. Chem. Soc. 145, 20716–20732 (2023).ArticleÂ
PubMedÂ
Google ScholarÂ
Pramanik, M. M. D., Qian, H., Xiao, W.-J. & Chen, J.-R. Photoinduced strategies towards strained molecules. Org. Chem. Front. 7, 2531–2537 (2020).ArticleÂ
Google ScholarÂ
He, F.-S., Xie, S., Yao, Y. & Wu, J. Recent advances in the applications of [1.1.1]propellane in organic synthesis. Chin. Chem. Lett. 31, 3065–3072 (2020).ArticleÂ
Google ScholarÂ
Kanazawa, J. & Uchiyama, M. Recent advances in the synthetic chemistry of bicyclo[1.1.1]pentane. Synlett 30, 1–11 (2019).ArticleÂ
Google ScholarÂ
Huang, W., Keess, S. & Molander, G. A. A general and practical route to functionalized bicyclo[1.1.1]pentane-heteroaryls enabled by photocatalytic multicomponent heteroarylation of [1.1.1]propellane. Angew. Chem. Int. Ed. 62, e202302223 (2023).ArticleÂ
Google ScholarÂ
Gao, Y. et al. Visible light-induced synthesis of 1,3-disubstituted bicyclo[1.1.1]pentane ketones via cooperative photoredox and N-heterocyclic carbene catalysis. Green. Chem. 25, 3909–3915 (2023).ArticleÂ
Google ScholarÂ
Dong, W., Keess, S. & Molander, G. A. Nickel-mediated alkyl-, acyl-, and sulfonylcyanation of [1.1.1]propellane. Chem. Catal. 3, 100608 (2023).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Pickford, H. D. et al. Rapid and scalable halosulfonylation of strain-release reagents. Angew. Chem. Int. Ed. 62, e202213508 (2023).ArticleÂ
Google ScholarÂ
Huang, W., Keess, S. & Molander, G. A. One step synthesis of unsymmetrical 1,3-disubstituted BCP ketones via nickel/photoredox-catalyzed [1.1.1]propellane multicomponent dicarbofunctionalization. Chem. Sci. 13, 11936–11942 (2022).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Dong, W. et al. Exploiting the sp2 character of bicyclo[1.1.1]pentyl radicals in the transition-metal-free multi-component difunctionalization of [1.1.1]propellane. Nat. Chem. 14, 1068–1077 (2022).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Huang, W., Keess, S. & Molander, G. A. Dicarbofunctionalization of [1.1.1]propellane enabled by nickel/photoredox dual catalysis: One-step multicomponent strategy for the synthesis of BCP-aryl derivatives. J. Am. Chem. Soc. 144, 12961–12969 (2022).ArticleÂ
PubMedÂ
Google ScholarÂ
Livesley, S. et al. Electrophilic activation of [1.1.1]propellane for the synthesis of nitrogen-substituted bicyclo[1.1.1]pentanes. Angew. Chem. Int. Ed. 61, e202111291 (2022).ArticleÂ
ADSÂ
Google ScholarÂ
Nugent, J., Sterling, A. J., Frank, N., Mousseau, J. J. & Anderson, E. A. Synthesis of α-quaternary bicyclo[1.1.1]pentanes through synergistic organophotoredox and hydrogen atom transfer catalysis. Org. Lett. 23, 8628–8633 (2021).ArticleÂ
PubMedÂ
Google ScholarÂ
Wei, Y. et al. Radical carbosulfonylation of propellane: synthesis of sulfonyl β-keto-bicyclo[1,1,1]pentanes. Synthesis 53, 3325–3332 (2021).ArticleÂ
Google ScholarÂ
Pickford, H. D. et al. Twofold radical-based synthesis of n,c-difunctionalized bicyclo[1.1.1]pentanes. J. Am. Chem. Soc. 143, 9729–9736 (2021).ArticleÂ
PubMedÂ
Google ScholarÂ
Wu, Z., Xu, Y., Zhang, H., Wu, X. & Zhu, C. Radical-mediated sulfonyl alkynylation, allylation, and cyanation of propellane. Chem. Commun. 57, 6066–6069 (2021).ArticleÂ
Google ScholarÂ
Shin, S., Lee, S., Choi, W., Kim, N. & Hong, S. Visible-light-induced 1,3-aminopyridylation of [1.1.1]propellane with n-aminopyridinium salts. Angew. Chem. Int. Ed. 60, 7873–7879 (2021).ArticleÂ
Google ScholarÂ
Wu, Z., Xu, Y., Wu, X. & Zhu, C. Synthesis of selenoether and thioether functionalized bicyclo[1.1.1]pentanes. Tetrahedron 76, 131692 (2020).ArticleÂ
Google ScholarÂ
Zhang, X. et al. Copper-mediated synthesis of drug-like bicyclopentanes. Nature 580, 220–226 (2020).ArticleÂ
ADSÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Yu, S., Jing, C., Noble, A. & Aggarwal, V. K. 1,3-Difunctionalizations of [1.1.1]propellane via 1,2-metallate rearrangements of boronate complexes. Angew. Chem. Int. Ed. 59, 3917–3921 (2020).ArticleÂ
Google ScholarÂ
Gianatassio, R. et al. Organic chemistry. strain-release amination. Science 351, 241–246 (2016).ArticleÂ
ADSÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Shin, S., Kim, Y. & Hong, S. Three-component cyclobutylation via silver(I)-catalyzed carbene transfer reactions with [1.1.1]propellane. ACS Catal. 13, 13325–13332 (2023).ArticleÂ
Google ScholarÂ
Yu, S., Noble, A., Bedford, R. B. & Aggarwal, V. K. Methylenespiro[2.3]hexanes via nickel-catalyzed cyclopropanations with [1.1.1]propellane. J. Am. Chem. Soc. 141, 20325–20334 (2019).ArticleÂ
PubMedÂ
Google ScholarÂ
Lasányi, D. & Tolnai, G. L. Copper-catalyzed ring opening of [1.1.1]propellane with alkynes: Synthesis of exocyclic allenic cyclobutanes. Org. Lett. 21, 10057–10062 (2019).ArticleÂ
PubMedÂ
Google ScholarÂ
Du, X., Xu, D., Xu, G., Yu, C. & Jiang, X. Synthesis of imidized cyclobutene derivatives by strain release of [1.1.1]propellane. Org. Lett. 24, 7323–7327 (2022).ArticleÂ
PubMedÂ
Google ScholarÂ
Adcock, J. L. & Gakh, A. A. Nucleophilic substitution in 1-substituted 3-iodobicyclo[1.1.1]pentanes. a new synthetic route to functionalized bicyclo[1.1.1]pentane derivatives. J. Org. Chem. 57, 6206–6210 (1992).ArticleÂ
Google ScholarÂ
Wiberg, K. B. & Walker, F. H. [1.1.1]propellane. J. Am. Chem. Soc. 104, 5239–5240 (1982).ArticleÂ
Google ScholarÂ
Shelp, R., Merchant, R. R., Hughes, J. M. E. & Walsh, P. J. Enantioenriched BCP benzylamine synthesis via metal hydride hydrogen atom transfer/sulfinimine addition to [1.1.1]propellane. Org. Lett. 24, 110–114 (2022).ArticleÂ
PubMedÂ
Google ScholarÂ
Matos, J. L. M., Vásquez-Céspedes, S., Gu, J., Oguma, T. & Shenvi, R. A. Branch-selective addition of unactivated olefins into imines and aldehydes. J. Am. Chem. Soc. 140, 16976–16981 (2018).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Quint, V. et al. Transition metal-free regioselective phosphonation of pyridines: scope and mechanism. ACS Org. Inorg. Au 3, 151–157 (2023).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Mathi, G. R., Kweon, B., Moon, Y., Jeong, Y. & Hong, S. Regioselective C-H functionalization of heteroarene n-oxides enabled by a traceless nucleophile. Angew. Chem. Int. Ed. 59, 22675–22683 (2020).ArticleÂ
Google ScholarÂ
Wang, J. et al. E-selective radical difunctionalization of unactivated alkynes: preparation of functionalized allyl alcohols from aliphatic alkynes. Adv. Sci. 11, e2309022 (2024).ArticleÂ
Google ScholarÂ
Lei, Z., Zhang, W. & Wu, J. Photocatalytic hydrogen atom transfer-induced arbuzov-type α-C(sp3)–H phosphonylation of aliphatic amines. ACS Catal. 13, 16105–16113 (2023).ArticleÂ
Google ScholarÂ
Wei, Y., Wu, X., Chen, Y. & Zhu, C. Radical-polar crossover allenylation of alkenes: Divergent synthesis of homoallenic alcohols and amides. Chem. Catal. 3, 100551 (2023).ArticleÂ
Google ScholarÂ
Das, M., Zamani, L., Bratcher, C. & Musacchio, P. Z. Azolation of benzylic C-H bonds via photoredox-catalyzed carbocation generation. J. Am. Chem. Soc. 145, 3861–3868 (2023).ArticleÂ
Google ScholarÂ
Wu, X. et al. 11C, 12C and 13C-cyanation of electron-rich arenes via organic photoredox catalysis. Chem 9, 343–362 (2023).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Murray, P. R. D. et al. Radical redox annulations: a general light-driven method for the synthesis of saturated heterocycles. ACS Catal. 12, 13732–13740 (2022).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Bi, M.-H., Cheng, Y., Xiao, W.-J. & Chen, J.-R. Visible-light-induced photoredox-catalyzed selective 1,4-difluoroalkylesterification of 1-aryl-1,3-dienes. Org. Lett. 24, 7589–7594 (2022).ArticleÂ
PubMedÂ
Google ScholarÂ
Leibler, I. N.-M., Tekle-Smith, M. A. & Doyle, A. G. A general strategy for C(sp3)–H functionalization with nucleophiles using methyl radical as a hydrogen atom abstractor. Nat. Commun. 12, 1–10 (2021).ArticleÂ
Google ScholarÂ
Chen, W. et al. Direct arene C-H fluorination with 18F- via organic photoredox catalysis. Science 364, 1170–1174 (2019).ArticleÂ
ADSÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Li, G.-X. et al. A unified photoredox-catalysis strategy for C(sp3)-H hydroxylation and amidation using hypervalent iodine. Chem. Sci. 8, 7180–7185 (2017).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
McManus, J. B. & Nicewicz, D. A. Direct C-H cyanation of arenes via organic photoredox catalysis. J. Am. Chem. Soc. 139, 2880–2883 (2017).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Xia, J.-B., Zhu, C. & Chen, C. Visible light-promoted metal-free sp3-C–H fluorination. Chem. Commun. 50, 11701–11704 (2014).ArticleÂ
Google ScholarÂ
Michaudel, Q., Thevenet, D. & Baran, P. S. Intermolecular Ritter-type C-H amination of unactivated sp3 carbons. J. Am. Chem. Soc. 134, 2547–2550 (2012).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Shevick, S. L. et al. Catalytic hydrogen atom transfer to alkenes: a roadmap for metal hydrides and radicals. Chem. Sci. 11, 12401–12422 (2020).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Green, S. A. et al. The high chemofidelity of metal-catalyzed hydrogen atom transfer. Acc. Chem. Res. 51, 2628–2640 (2018).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Crossley, S. W. M., Obradors, C., Martinez, R. M. & Shenvi, R. A. Mn-, Fe-, and co-catalyzed radical hydrofunctionalizations of olefins. Chem. Rev. 116, 8912–9000 (2016).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Shibutani, S., Nagao, K. & Ohmiya, H. A dual cobalt and photoredox catalysis for hydrohalogenation of alkenes. J. Am. Chem. Soc. 146, 4375–4379 (2024).ArticleÂ
PubMedÂ
Google ScholarÂ
Kong, L., Gan, X.-C., van der Puyl Lovett, V. A. & Shenvi, R. A. Alkene hydrobenzylation by a single catalyst that mediates iterative outer-sphere steps. J. Am. Chem. Soc. 146, 2351–2357 (2024).ArticleÂ
PubMedÂ
Google ScholarÂ
Banjare, S. K. et al. Access to polyheterocyclic compounds through iron(ii)-mediated radical cascade cyclization utilizing 2-ethynylbenzaldehydes and aryl isonitriles. Org. Lett. 25, 6424–6428 (2023).ArticleÂ
PubMedÂ
Google ScholarÂ
Takekawa, Y., Nakagawa, M., Nagao, K. & Ohmiya, H. A quadruple catalysis enabling intermolecular branch-selective hydroacylation of styrenes. Chemistry 29, e202301484 (2023).ArticleÂ
PubMedÂ
Google ScholarÂ
Nakagawa, M., Matsuki, Y., Nagao, K. & Ohmiya, H. A triple photoredox/cobalt/brønsted acid catalysis enabling markovnikov hydroalkoxylation of unactivated alkenes. J. Am. Chem. Soc. 144, 7953–7959 (2022).ArticleÂ
PubMedÂ
Google ScholarÂ
Green, S. A., Huffman, T. R., McCourt, R. O., van der Puyl, V. & Shenvi, R. A. Hydroalkylation of olefins to form quaternary carbons. J. Am. Chem. Soc. 141, 7709–7714 (2019).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Ma, X., Dang, H., Rose, J. A., Rablen, P. & Herzon, S. B. Hydroheteroarylation of unactivated alkenes using n-methoxyheteroarenium salts. J. Am. Chem. Soc. 139, 5998–6007 (2017).ArticleÂ
PubMedÂ
Google ScholarÂ
Ma, X. & Herzon, S. B. Intermolecular hydropyridylation of unactivated alkenes. J. Am. Chem. Soc. 138, 8718–8721 (2016).ArticleÂ
PubMedÂ
Google ScholarÂ
Qin, J. et al. Photoinduced cobalt catalysis for the reductive coupling of pyridines and dienes enabled by paired single-electron transfer. Angew. Chem. Int. Ed. 62, e202310639 (2023).ArticleÂ
Google ScholarÂ
Bergamaschi, E., Mayerhofer, V. J. & Teskey, C. J. Light-driven cobalt hydride catalyzed hydroarylation of styrenes. ACS Catal. 12, 14806–14811 (2022).ArticleÂ
Google ScholarÂ
Wu, X. et al. Intercepting hydrogen evolution with hydrogen-atom transfer: electron-initiated hydrofunctionalization of alkenes. J. Am. Chem. Soc. 144, 17783–17791 (2022).ArticleÂ
PubMedÂ
Google ScholarÂ
Liang, B., Wang, Q. & Liu, Z.-Q. A Fe(III)/NaBH4-promoted free-radical hydroheteroarylation of alkenes. Org. Lett. 19, 6463–6465 (2017).ArticleÂ
PubMedÂ
Google ScholarÂ
Lo, J. C. et al. Fe-catalyzed C-C bond construction from olefins via radicals. J. Am. Chem. Soc. 139, 2484–2503 (2017).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Greenwood, J. W., Boyle, B. T. & McNally, A. Pyridylphosphonium salts as alternatives to cyanopyridines in radical-radical coupling reactions. Chem. Sci. 12, 10538–10543 (2021).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Jung, J., Kim, J., Park, G., You, Y. & Cho, E. J. Selective debromination and α-hydroxylation of α-bromo ketones using Hantzsch esters as photoreductants. Adv. Synth. Catal. 358, 74–80 (2016).ArticleÂ
Google ScholarÂ
Tan, C.-Y., Kim, M., Park, I., Kim, Y. & Hong, S. Site-selective pyridine c-h alkylation with alcohols and thiols via single-electron transfer of frustrated lewis pairs. Angew. Chem. Int. Ed. 61, e202213857 (2022).ArticleÂ
Google ScholarÂ
Kim, C., Jeong, J., Vellakkaran, M. & Hong, S. Photocatalytic decarboxylative pyridylation of carboxylic acids using in situ-generated amidyl radicals as oxidants. ACS Catal. 12, 13225–13233 (2022).ArticleÂ
Google ScholarÂ
Kim, M., Koo, Y. & Hong, S. N-functionalized pyridinium salts: a new chapter for site-selective pyridine C–H functionalization via radical-based processes under visible light irradiation. Acc. Chem. Res. 55, 3043–3056 (2022).ArticleÂ
PubMedÂ
Google ScholarÂ
Kim, M., You, E., Kim, J. & Hong, S. Site-selective pyridylic C-H functionalization by photocatalytic radical cascades. Angew. Chem. Int. Ed. 61, e202204217 (2022).ArticleÂ
ADSÂ
Google ScholarÂ
Choi, H., Mathi, G. R., Hong, S. & Hong, S. Enantioselective functionalization at the C4 position of pyridinium salts through NHC catalysis. Nat. Commun. 13, 1776 (2022).ArticleÂ
ADSÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Lee, W., Jung, S., Kim, M. & Hong, S. Site-selective direct C-H pyridylation of unactivated alkanes by triplet excited anthraquinone. J. Am. Chem. Soc. 143, 3003–3012 (2021).ArticleÂ
PubMedÂ
Google ScholarÂ
Cao, H., Bhattacharya, D., Cheng, Q. & Studer, A. C-H functionalization of pyridines via oxazino pyridine intermediates: switching to para-selectivity under acidic conditions. J. Am. Chem. Soc. 145, 15581–15588 (2023).ArticleÂ
PubMedÂ
Google ScholarÂ
Vellakkaran, M., Kim, T. & Hong, S. Visible-light-induced c4-selective functionalization of pyridinium salts with cyclopropanols. Angew. Chem. Int. Ed. 61, e202113658 (2022).ArticleÂ
Google ScholarÂ
Jung, S., Shin, S., Park, S. & Hong, S. Visible-light-driven c4-selective alkylation of pyridinium derivatives with alkyl bromides. J. Am. Chem. Soc. 142, 11370–11375 (2020).ArticleÂ
PubMedÂ
Google ScholarÂ
Moon, Y. et al. Visible light induced alkene aminopyridylation using N-aminopyridinium salts as bifunctional reagents. Nat. Commun. 10, 4117 (2019).ArticleÂ
ADSÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Kim, D., Rahaman, S. M. W., Mercado, B. Q., Poli, R. & Holland, P. L. Roles of iron complexes in catalytic radical alkene cross-coupling: a computational and mechanistic study. J. Am. Chem. Soc. 141, 7473–7485 (2019).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Gan, X.-C. et al. Iron-catalyzed hydrobenzylation: stereoselective synthesis of (-)-eugenial C. J. Am. Chem. Soc. 145, 15714–15720 (2023).ArticleÂ
PubMedÂ
Google ScholarÂ
Zhang, C., He, Y. & An, G. Iron-mediated divergent reductive coupling reactions of heteroarenes with alkenes. Org. Chem. Front. 10, 2318–2323 (2023).ArticleÂ
Google ScholarÂ
Karnik, A. V. & Hasan, M. Conformations Of Cyclic, Fused And Bridged Ring Molecules. in Stereochemistry (eds. Karnik, A. V. & Hasan, M.) Ch. 8 (Elsevier, 2021).Ni, S.-F. et al. Recent advances in γ-C(sp3)–H bond activation of amides, aliphatic amines, sulfanilamides and amino acids. Coord. Chem. Rev. 455, 214255 (2022).ArticleÂ
Google ScholarÂ
CzerwiÅ„ski, P. J. & Furman, B. Reductive functionalization of amides in synthesis and for modification of bioactive compounds. Front Chem. 9, 655849 (2021).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Huang, Z., Lim, H. N., Mo, F., Young, M. C. & Dong, G. Transition metal-catalyzed ketone-directed or mediated C-H functionalization. Chem. Soc. Rev. 44, 7764–7786 (2015).ArticleÂ
PubMedÂ
Google ScholarÂ
Liu, H., Laporte, A. G., Tardieu, D., Hazelard, D. & Compain, P. Formal glycosylation of quinones with exo-glycals enabled by iron-mediated oxidative radical-polar crossover. J. Org. Chem. 87, 13178–13194 (2022).ArticleÂ
PubMedÂ
Google ScholarÂ
Saavedra, B. & Ramón, D. J. Deep eutectic solvent as a sustainable medium for c–c bond formation via multicomponent radical conjugate additions. ACS Sustain. Chem. Eng. 9, 7941–7947 (2021).ArticleÂ
Google ScholarÂ
Tardieu, D. et al. Stereoselective synthesis of C,C-glycosides from exo-glycals enabled by iron-mediated hydrogen atom transfer. Org. Lett. 21, 7262–7267 (2019).ArticleÂ
PubMedÂ
Google ScholarÂ
Lo, J. C., Yabe, Y. & Baran, P. S. A practical and catalytic reductive olefin coupling. J. Am. Chem. Soc. 136, 1304–1307 (2014).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Chinchole, A., Henriquez, M. A., Cortes-Arriagada, D., Cabrera, A. R. & Reiser, O. Iron(III)-light-induced homolysis: a dual photocatalytic approach for the hydroacylation of alkenes using acyl radicals via direct HAT from aldehydes. ACS Catal. 12, 13549–13554 (2022).ArticleÂ
Google ScholarÂ
Yan, J. et al. Divergent functionalization of aldehydes photocatalyzed by neutral eosin Y with sulfone reagents. Nat. Commun. 12, 7214 (2021).ArticleÂ
ADSÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Jung, S., Lee, H., Moon, Y., Jung, H.-Y. & Hong, S. Site-selective c–h acylation of pyridinium derivatives by photoredox catalysis. ACS Catal. 9, 9891–9896 (2019).ArticleÂ
Google ScholarÂ
Arnett, E. M. & Wu, C. Y. Base strengths of some aliphatic ethers in aqueous sulfuric acid. J. Am. Chem. Soc. 84, 1680–1684 (1962).ArticleÂ
Google ScholarÂ