Johansson Seechurn, C. C. C., Kitching, M. O., Colacot, T. J. & Snieckus, V. Palladium-catalyzed cross-coupling: A historical contextual perspective to the 2010 Nobel Prize. Angew. Chem. Int. Ed. 51, 5062–5085 (2012).Article
CAS
Google Scholar
Negishi, E.-I. Transition metal-catalyzed organometallic reactions that have revolutionized organic synthesis. Bull. Chem. Soc. Jpn. 80, 233–257 (2007).Article
CAS
Google Scholar
de Meijere, A. & Diederich, F. Eds., Metal-catalyzed cross-coupling reactions, 2nd ed. (Wiley-VCH, 2004).Roughley, S. D. & Jordan, A. M. The medicinal chemist’s toolbox: An analysis of reactions used in the pursuit of drug candidates. J. Med. Chem. 54, 3451–3479 (2011).Article
CAS
PubMed
Google Scholar
Choi, J. & Fu, G. C. Transition metal–catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry. Science 356, eaaf7230 (2017).Article
PubMed
PubMed Central
Google Scholar
Kranthikumar, R. Recent advances in C(sp3)−C(sp3) cross-coupling chemistry: A dominant performance of nickel catalysts. Organometallics 41, 667–679 (2022).Article
CAS
Google Scholar
Wu, D. et al. Alkene 1,1-difunctionalizations via organometallic-radical relay. Nat. Catal. 6, 1030–1041 (2023).Article
CAS
Google Scholar
Zeng, X. Recent advances in catalytic sequential reactions involving hydroelement addition to carbon–carbon multiple bonds. Chem. Rev. 113, 6864–6900 (2013).Article
CAS
PubMed
Google Scholar
Xia, Y., Qiu, D. & Wang, J. Transition-metal-catalyzed cross-couplings through carbene migratory insertion. Chem. Rev. 117, 13810–13889 (2017).Article
CAS
PubMed
Google Scholar
Zhao, G., Wu, Y., Wu, H.-H., Yang, J. & Zhang, J. Pd/GF-Phos-catalyzed asymmetric three-component coupling reaction to access chiral diarylmethyl alkynes. J. Am. Chem. Soc. 143, 17983–17988 (2021).Article
CAS
PubMed
Google Scholar
Wu, X. et al. Modular α-tertiary amino ester synthesis through cobalt-catalysed asymmetric aza-Barbier reaction. Nat. Chem. 16, 398–407 (2024).Xu, H. et al. Highly enantioselective copper- and iron-catalyzed intramolecular cyclopropanation of indoles. J. Am. Chem. Soc. 139, 7697–7700 (2017).Article
CAS
PubMed
Google Scholar
Bykowski, D., Wu, K.-H. & Doyle, M. P. Vinyldiazolactone as a vinylcarbene precursor: highly selective C−H insertion and cyclopropanation reactions. J. Am. Chem. Soc. 128, 16038–16039 (2006).Article
CAS
PubMed
PubMed Central
Google Scholar
Xia, Y. & Wang, J. Transition-metal-catalyzed cross-coupling with ketones or aldehydes via N-tosylhydrazones. J. Am. Chem. Soc. 142, 10592–10605 (2020).Article
CAS
PubMed
Google Scholar
Li, M.-L., Yu, J.-H., Li, Y.-H., Zhu, S.-F. & Zhou, Q.-L. Highly enantioselective carbene insertion into N-H bonds of aliphatic amines. Science 366, 990–994 (2019).Article
ADS
CAS
PubMed
Google Scholar
Fischer, E. O. & Maasböl, A. On the existence of a tungsten carbonyl carbene complex. Angew. Chem. Int. Ed. 3, 580–581 (1964).Article
Google Scholar
Zhou, G., Guo, Z. & Shen, X. Electron-rich oxycarbenes: new synthetic and catalytic applications beyond group 6 Fischer carbene complexes. Angew. Chem. Int. Ed. 62, e202217189 (2023).Article
CAS
Google Scholar
Sakurai, S., Inagaki, T., Kodama, T., Yamanaka, M. & Tobisu, M. Palladium-catalyzed siloxycyclopropanation of alkenes using acylsilanes. J. Am. Chem. Soc. 144, 1099–1105 (2022).Article
CAS
PubMed
Google Scholar
Palomo, E. et al. Generating Fischer-type Rh-carbenes with Rh-carbynoids. J. Am. Chem. Soc. 145, 4975–4981 (2023).Article
CAS
PubMed
PubMed Central
Google Scholar
Green, S. P. et al. Thermal stability and explosive hazard assessment of diazo compounds and diazo transfer reagents. Org. Process Res. Dev. 24, 67–84 (2020).Article
CAS
PubMed
Google Scholar
Bijoy, R., Agarwala, P., Roy, L. & Thorat, B. N. Unconventional ethereal solvents in organic chemistry: a perspective on applications of 2-methyltetrahydrofuran, cyclopentyl methyl ether, and 4-methyltetrahydropyran. Org. Process Res. Dev. 26, 480–492 (2022).Article
CAS
Google Scholar
Li, C.-J. Cross-dehydrogenative coupling (CDC): exploring C-C bond formations beyond functional group transformations. Acc. Chem. Res. 42, 335–344 (2009).Article
CAS
PubMed
Google Scholar
Liu, C. et al. Oxidative coupling between two hydrocarbons: an update of recent C–H functionalizations. Chem. Rev. 115, 12138–12204 (2015).Article
ADS
CAS
PubMed
Google Scholar
Ji, C.-L. et al. Photoinduced gold-catalyzed divergent dechloroalkylation of gem-dichloroalkanes. Nat. Catal. 5, 1098–1109 (2022).Article
CAS
Google Scholar
Hu, M.-Y., Lian, J., Sun, W., Qiao, T.-Z. & Zhu, S.-F. Iron-catalyzed dihydrosilylation of alkynes: efficient access to geminal bis(silanes). J. Am. Chem. Soc. 141, 4579–4583 (2019).Article
CAS
PubMed
Google Scholar
Tan, Y.-X. et al. Ruthenium-catalyzed geminal hydroborative cyclization of enynes. Angew. Chem. Int. Ed. 61, e202204319 (2022).Article
ADS
CAS
Google Scholar
Bullock, R. M. et al. Using nature’s blueprint to expand catalysis with earth-abundant metals. Science 369, eabc3183 (2020).Article
CAS
PubMed
PubMed Central
Google Scholar
Soleilhavoup, M. & Bertrand, G. Cyclic (alkyl)(amino)carbenes (CAACs): stable carbenes on the rise. Acc. Chem. Res. 48, 256–266 (2015).Article
CAS
PubMed
Google Scholar
Hopkinson, M. N., Richter, C., Schedler, M. & Glorius, F. An overview of N-heterocyclic carbenes. Nature 510, 485–496 (2014).Article
ADS
CAS
PubMed
Google Scholar
Bellotti, P., Koy, M., Hopkinson, M. N. & Glorius, F. Recent advances in the chemistry and applications of N-heterocyclic carbenes. Nat. Rev. Chem. 5, 711–725 (2021).Article
CAS
PubMed
Google Scholar
Zhao, L. & Zeng, X. Transition-metal-catalyzed reactions promoted by cyclic (alkyl or aryl)(amino)carbene ligands. Chem 8, 2082–2113 (2022).Article
CAS
Google Scholar
Li, J. & Knochel, P. Chromium-catalyzed cross-couplings and related reactions. Synthesis 51, 2100–2106 (2019).Article
CAS
Google Scholar
Cong, X. & Zeng, X. Mechanistic diversity of low-valent chromium catalysis: cross-coupling and hydrofunctionalization. Acc. Chem. Res. 54, 2014–2026 (2021).Article
CAS
PubMed
Google Scholar
Zhang, Y. & Li, C.-J. DDQ-mediated direct cross-dehydrogenative-coupling (CDC) between benzyl ethers and simple ketones. J. Am. Chem. Soc. 128, 4242–4243 (2006).Article
CAS
PubMed
Google Scholar
Liu, D., Liu, C., Li, H. & Lei, A. Direct functionalization of tetrahydrofuran and 1,4-dioxane: nickel-catalyzed oxidative C(sp3)–H arylation. Angew. Chem. Int. Ed. 52, 4453–4456 (2013).Article
CAS
Google Scholar
Qvortrup, K., Rankic, D. A. & MacMillan, D. W. C. A general strategy for organocatalytic activation of C–H bonds via photoredox catalysis: Direct arylation of benzylic ethers. J. Am. Chem. Soc. 136, 626–629 (2014).Article
CAS
PubMed
Google Scholar
Xu, S. et al. Enantioselective C(sp3)−H functionalization of oxacycles via photo-HAT/nickel dual catalysis. J. Am. Chem. Soc. 145, 5231–5241 (2023).Article
CAS
PubMed
Google Scholar
Huang, H., Strater, Z. M. & Lambert, T. H. Electrophotocatalytic C−H functionalization of ethers with high regioselectivity. J. Am. Chem. Soc. 142, 1698–1703 (2020).Article
CAS
PubMed
PubMed Central
Google Scholar
Ye, B., Zhao, J., Zhao, K., McKenna, J. M. & Toste, F. D. Chiral diaryliodonium phosphate enables light driven diastereoselective α‐C(sp3)−H acetalization. J. Am. Chem. Soc. 140, 8350–8356 (2018).Article
CAS
PubMed
PubMed Central
Google Scholar
Hatanaka, Y. & Hiyama, T. Cross-coupling of organosilanes with organic halides mediated by palladium catalyst and tris(diethy1amino)sulfonium difluorotrimethylsilicate. J. Org. Chem. 53, 918–920 (1988).Article
CAS
Google Scholar
Tamao, K., Akita, M. & Kumada, M. Hydrogen peroxide oxidation of the silicon-carbon bond in organoalkoxysllanes. Organometallics 2, 1696–1698 (1983).Article
Google Scholar
Xiao, W. & Wu, J. Narasaka reaction: Desilylative acylation of 1-alkenylsilanes with acid anhydrides. Chin. Chem. Lett. 32, 2751–2755 (2021).Article
CAS
Google Scholar
He, R. et al. Mn-catalyzed three-component reactions of imines/nitriles, Grignard reagents, and tetrahydrofuran: An expedient access to 1,5-amino/keto alcohols. J. Am. Chem. Soc. 136, 6558–6561 (2014).Article
CAS
PubMed
Google Scholar
Steib, A. K., Kuzmina, O. M., Fernandez, S., Flubacher, D. & Knochel, P. Efficient chromium(II)-catalyzed cross-coupling reactions between Csp2 Centers. J. Am. Chem. Soc. 135, 15346–15349 (2013).Article
CAS
PubMed
Google Scholar
Schwarz, J. L., Schäfers, F., Tlahuext-Aca, A., Lückemeier, L. & Glorius, F. Diastereoselective allylation of aldehydes by dual photoredox and chromium catalysis. J. Am. Chem. Soc. 140, 12705–12709 (2018).Article
CAS
PubMed
Google Scholar
Liu, H.-L., Wang, X., Gao, K. & Wang, Z. Catalytic diastereo- and enantioselective cyclopropanation of gem-dihaloalkanes and terminal olefins. Angew. Chem. Int. Ed. 62, e202305987 (2023).Article
CAS
Google Scholar
Schwarz, J. L., Kleinmans, R., Paulisch, T. O. & Glorius, F. 1,2-Amino alcohols via Cr/photoredox dual-catalyzed addition of α-amino carbanion equivalents to carbonyls. J. Am. Chem. Soc. 142, 2168–2174 (2020).Article
CAS
PubMed
Google Scholar
Fan, F. et al. Chemoselective chromium-catalysed cross-coupling enables three-component tertiary alkane synthesis. Nat. Synth. 2, 1046–1058 (2023).Article
ADS
Google Scholar
Chu, J., Munz, D., Jazzar, R., Melaimi, M. & Bertrand, G. Synthesis of hemilabile cyclic (alkyl)(amino)carbenes (CAACs) and applications in organometallic chemistry. J. Am. Chem. Soc. 138, 7884–7887 (2016).Article
CAS
PubMed
Google Scholar
Gao, Y. et al. Cyclic (alkyl)(amino)carbene ligands enable Cu-catalyzed Markovnikov protoborationand protosilylation of terminal alkynes: A versatile portal to functionalized alkenes. Angew. Chem. Int. Ed. 60, 19871–19878 (2021).Article
CAS
Google Scholar
Zhao, L. et al. Cyclic (alkyl)(amino)carbene ligand-promoted nitro deoxygenative hydroboration with chromium catalysis: Scope, mechanism, and applications. J. Am. Chem. Soc. 143, 1618–1629 (2021).Article
CAS
PubMed
Google Scholar
Ling, L. et al. Chromium-catalyzed stereodivergent E- and Z-selective alkyne hydrogenation controlled by cyclic (alkyl)(amino)carbene ligands. Nat. Commun. 14, 990 (2023).Article
ADS
CAS
PubMed
PubMed Central
Google Scholar
Li, N., Li, Y., Wu, X., Zhu, C. & Xie, J. Radical deuteration. Chem. Soc. Rev. 51, 6291–6306 (2022).Article
CAS
PubMed
Google Scholar
Albahily, K. et al. Vinyl oxidative coupling as a synthetic route to catalytically active monovalent chromium. J. Am. Chem. Soc. 133, 6388–6395 (2011).Article
CAS
PubMed
Google Scholar
Zhang, Z. & Wang, J. Recent studies on the reactions of α-diazocarbonyl compounds. Tetrahedron 64, 6577–6605 (2008).Article
CAS
Google Scholar