Tyman, J. H. Synthetic and Natural Phenols (Elsevier, 1996).

Huang, Z. & Lumb, J.-P. Phenol-directed C–H functionalization. ACS Catal. 9, 521–555 (2019).

Article  CAS  Google Scholar 

Hesse, W. & Lang, J. Phenolic resins. Ullmann’s Encycl. Ind. Chem. 26, 583–600 (2011).

Google Scholar 

Scott, K. A., Cox, P. B. & Njardarson, J. T. Phenols in pharmaceuticals: analysis of a recurring motif. J. Med. Chem. 65, 7044–7072 (2022).

Article  CAS  PubMed  Google Scholar 

Foti, M. C. Antioxidant properties of phenols. J. Pharm. Pharmacol. 59, 1673–1685 (2010).

Article  Google Scholar 

Burley, S. K. & Petsko, G. A. Aromatic–aromatic interaction: a mechanism of protein structure stabilization. Science 229, 23–28 (1985).

Article  CAS  PubMed  Google Scholar 

Manglik, A. et al. Crystal structure of the µ-opioid receptor bound to a morphinan antagonist. Nature 485, 321–326 (2012).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Qiu, Z. & Li, C.-J. Transformations of less-activated phenols and phenol derivatives via C–O cleavage. Chem. Rev. 120, 10454–10515 (2020).

Article  CAS  PubMed  Google Scholar 

Quideau, S., Deffieux, D. & Pouységu, L. in Comprehensive Organic Synthesis (Second Edition) (ed. Knochel, P.) 656–740 (Elsevier, 2014).

Pouységu, L., Deffieux, D. & Quideau, S. Hypervalent iodine-mediated phenol dearomatization in natural product synthesis. Tetrahedron 66, 2235–2261 (2010).

Article  Google Scholar 

Gross, K. C. & Seybold, P. G. Substituent effects on the physical properties and pKa of phenol. Int. J. Quantum Chem. 85, 569–579 (2001).

Article  CAS  Google Scholar 

Bertin, C. et al. Grass roots chemistry: meta-tyrosine, an herbicidal nonprotein amino acid. Proc. Natl Acad. Sci. USA 104, 16964–16969 (2007).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Tyminski, M., Ciacka, K., Staszek, P., Gniazdowska, A. & Krasuska, U. Toxicity of meta-tyrosine. Plants 10, 2800 (2021).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Izawa, Y., Pun, D. & Stahl, S. S. Palladium-catalyzed aerobic dehydrogenation of substituted cyclohexanones to phenols. Science 333, 209–213 (2011).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Izawa, Y., Zheng, C. & Stahl, S. S. Aerobic oxidative Heck/dehydrogenation reactions of cyclohexenones: efficient access to meta-substituted phenols. Angew. Chem. Int. Ed. 52, 3672–3675 (2013).

Article  CAS  Google Scholar 

Fier, P. S. & Maloney, K. M. Synthesis of complex phenols enabled by a rationally designed hydroxide surrogate. Angew. Chem. Int. Ed. 56, 4478–4482 (2017).

Article  CAS  Google Scholar 

Xu, J. et al. Highly efficient synthesis of phenols by copper-catalyzed oxidative hydroxylation of arylboronic acids at room temperature in water. Org. Lett. 12, 1964–1967 (2010).

Article  CAS  PubMed  Google Scholar 

Maleczka, R. E., Shi, F., Holmes, D. & Smith, M. R. C–H activation/borylation/oxidation: a one-pot unified route to meta-substituted phenols bearing ortho-/para-directing groups. J. Am. Chem. Soc. 125, 7792–7793 (2003).

Article  CAS  PubMed  Google Scholar 

Senior, A., Ruffell, K. & Ball, L. T. meta-Selective C–H arylation of phenols via regiodiversion of electrophilic aromatic substitution. Nat. Chem. 15, 386–394 (2023).

Article  CAS  PubMed  Google Scholar 

Li, Z. et al. A tautomeric ligand enables directed C–H hydroxylation with molecular oxygen. Science 372, 1452–1457 (2021).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Yuan, C. et al. Metal-free oxidation of aromatic carbon–hydrogen bonds through a reverse-rebound mechanism. Nature 499, 192–196 (2013).

Article  CAS  PubMed  Google Scholar 

Sang, R. et al. Site‐selective C–H oxygenation via aryl sulfonium salts. Angew. Chem. Int. Ed. 58, 16161–16166 (2019).

Article  CAS  Google Scholar 

Nilova, A., Campeau, L.-C., Sherer, E. C. & Stuart, D. R. Analysis of benzenoid substitution patterns in small molecule active pharmaceutical ingredients. J. Med. Chem. 63, 13389–13396 (2020).

Article  CAS  PubMed  Google Scholar 

Schnürch, M., Spina, M., Khan, A. F., Mihovilovic, M. D. & Stanetty, P. Halogen dance reactions—a review. Chem. Soc. Rev. 36, 1046–1057 (2007).

Article  PubMed  Google Scholar 

Matsushita, K., Takise, R., Muto, K. & Yamaguchi, J. Ester dance reaction on the aromatic ring. Sci. Adv. 6, eaba7614 (2020).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Nakahara, H. & Yamaguchi, J. Aryl dance reaction of arylbenzoheteroles. Org. Lett. 24, 8083–8087 (2022).

Article  CAS  PubMed  Google Scholar 

Bolton, A., Lanewala, M. & Pickert, P. Isomerization of tert-butylphenols using zeolite catalysts. J. Org. Chem. 33, 3415–3418 (1968).

Article  CAS  Google Scholar 

Jacquesy, J.-C. & Jouannetaud, M.-P. Mechanism of isomerization of ortho or para bromo phenols in superacids. Tetrahedron Lett. 23, 1673–1676 (1982).

Article  CAS  Google Scholar 

Cernak, T., Dykstra, K. D., Tyagarajan, S., Vachal, P. & Krska, S. W. The medicinal chemist’s toolbox for late stage functionalization of drug-like molecules. Chem. Soc. Rev. 45, 546–576 (2016).

Article  CAS  PubMed  Google Scholar 

Esguerra, K. V. N., Xu, W. & Lumb, J.-P. Unified synthesis of 1,2-oxy-aminoarenes via a bio-inspired phenol–amine coupling. Chem 2, 533–549 (2017).

Article  CAS  Google Scholar 

Esguerra, K. V. N. & Lumb, J.-P. A bioinspired catalytic aerobic functionalization of phenols: regioselective construction of aromatic C–N and C–O bonds. ACS Catal. 7, 3477–3482 (2017).

Article  CAS  Google Scholar 

Esguerra, K. V. N. & Lumb, J.-P. Synthesis of ortho-azophenols by formal dehydrogenative coupling of phenols and hydrazines or hydrazides. Eur. J. Chem. 23, 8596–8600 (2017).

Article  CAS  Google Scholar 

Esguerra, K. V. N., Fall, Y. & Lumb, J.-P. A biomimetic catalytic aerobic functionalization of phenols. Angew. Chem. Int. Ed. 53, 5877–5881 (2014).

Article  CAS  Google Scholar 

Magdziak, D., Rodriguez, A. A., Van De Water, R. W. & Pettus, T. R. R. Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX). Org. Lett. 4, 285–288 (2002).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Cava, M. P., Litle, R. L. & Napier, D. R. Condensed cyclobutane aromatic systems. V. The synthesis of some α-diazoindanones: ring contraction in the indane series. J. Am. Chem. Soc. 80, 2257–2263 (1958).

Article  CAS  Google Scholar 

Nematollahi, D., Rahchamani, R. & Malekzadeh, M. Electrochemical sulfonylation of 4-tert-butylcatechol. Synth. Commun. 33, 2269–2274 (2003).

Article  CAS  Google Scholar 

Kornblum, N., Cooper, G. D. & Taylor, J. E. The chemistry of diazo compounds. II. Evidence for a free radical chain mechanism in the reduction of diazonium salts by hypophosphorous acid. J. Am. Chem. Soc. 72, 3013–3021 (1950).

Article  CAS  Google Scholar 

Clews, J. et al. Novel heterocyclic betaines relevant to the mechanism of tyrosinase-catalysed oxidation of phenols. Chem. Commun. 77–78 (1998).

Clews, J. et al. Oxidative cyclisation of N,N-dialkylcatechol amines to heterocyclic betaines via o-quinones: synthetic, pulse radiolytic and enzyme studies. J. Chem. Soc. Perkin Trans. 1. 4306–4315 (2000).

Huang, Z. et al. A bio-inspired synthesis of oxindoles by catalytic aerobic dual C–H functionalization of phenols. Chem. Sci. 7, 358–369 (2016).

Article  CAS  PubMed  Google Scholar 

Kosoglou, T. et al. Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin. Pharmacokinet. 44, 467–494 (2005).

Article  CAS  PubMed  Google Scholar 

Mravljak, J., Sova, M., Ko-Vac, A., Gobec, S. & Casar, Z. Process for the synthesis of ezetimibe and intermediates useful therefor. Slovenia patent (2010).

Klingler, F. D. in Asymmetric Catalysis on Industrial Scale (eds Blaser, H. U., Federsel, H. J.) 171–185 (Wiley‐VCH, 2010).

Stewart, I., Newhall, W. F. & Edwards, G. J. The isolation and identification of l-synephrine in the leaves and fruit of citrus. J. Biol. Chem. 239, 930–932 (1964).

Article  CAS  Google Scholar 

Lu, T.-M., Ko, H.-H., Ng, L.-T. & Hsieh, Y.-P. Free-radical-scavenging, antityrosinase, and cellular melanogenesis inhibitory activities of synthetic isoflavones. Chem. Biodivers. 12, 963–979 (2015).

Article  CAS  PubMed  Google Scholar 

Zhang, Q., Tu, T., D’Avignon, D. A. & Gross, M. L. Balance of beneficial and del