[ad_1]
But, L. Privileged Buildings in Drug Discovery: Medicinal Chemistry and Synthesis 1st edn, 83–154 (Wiley, 2018).
Yoon, T. P. & Jacobsen, E. N. Privileged chiral catalysts. Science 299, 1691–1693 (2003).
Ashenhurst, J. A. Intermolecular oxidative cross-coupling of arenes. Chem. Soc. Rev. 39, 540–548 (2010).
Kozlowski, M. C. Oxidative coupling in complexity constructing transforms. Acc. Chem. Res. 50, 638–643 (2017).
Yang, Y., Lan, J. & You, J. Oxidative C–H/C–H coupling reactions between two (hetero)arenes. Chem. Rev. 117, 8787–8863 (2017).
Hüttel, W. & Müller, M. Regio- and stereoselective intermolecular phenol coupling enzymes in secondary metabolite biosynthesis. Nat. Prod. Rep. 38, 1011–1043 (2021).
Lunxiang, Y. & Liebscher, J. Carbon−carbon coupling reactions catalyzed by heterogeneous palladium catalysts. Chem. Rev. 107, 133–173 (2007).
Boström, J., Brown, D. G., Younger, R. J. & Keserü, G. M. Increasing the medicinal chemistry artificial toolbox. Nat. Rev. Drug Discov. 17, 709–727 (2018).
Yin, J., Rainka, M. P., Zhang, X.-X. & Buchwald, S. L. A extremely energetic Suzuki catalyst for the synthesis of sterically hindered biaryls: novel ligand coordination. J. Am. Chem. Soc. 124, 1162–1163 (2002).
Cammidge, A. N. & Crépy, Ok. V. L. Synthesis of chiral binaphthalenes utilizing the uneven Suzuki response. Tetrahedron 60, 4377–4386 (2004).
Martin, R. & Buchwald, S. L. Palladium-catalyzed Suzuki−Miyaura cross-coupling reactions using dialkylbiaryl phosphine ligands. Acc. Chem. Res. 41, 1461–1473 (2008).
Valente, C. et al. The event of cumbersome palladium NHC complexes for the most-challenging cross-coupling reactions. Angew. Chem. Int. Ed. 51, 3314–3332 (2012).
Patel, N. D. et al. Computationally assisted mechanistic investigation and growth of Pd-catalyzed uneven Suzuki–Miyaura and Negishi cross-coupling reactions for tetra-ortho-substituted biaryl synthesis. ACS Catal. 8, 10190–10209 (2018).
Ackermann, L., Potukuchi, H. Ok., Althammer, A., Born, R. & Mayer, P. Tetra-ortho-substituted biaryls by palladium-catalyzed Suzuki−Miyaura couplings with a diaminochlorophosphine ligand. Org. Lett. 12, 1004–1007 (2010).
Brown, D. G. & Boström, J. Evaluation of previous and current artificial methodologies on medicinal chemistry: the place have all the brand new reactions gone? J. Med. Chem. 59, 4443–4458 (2016).
Lee, Y. E., Cao, T., Torruellas, C. & Kozlowski, M. C. Selective oxidative homo- and cross-coupling of phenols with cardio catalysts. J. Am. Chem. Soc. 136, 6782–6785 (2014).
Nieves-Quinones, Y. et al. Chromium-salen catalyzed cross-coupling of phenols: mechanism and origin of the selectivity. J. Am. Chem. Soc. 141, 10016–10032 (2019).
Shalit, H., Dyadyuk, A. & Pappo, D. Selective oxidative phenol coupling by iron catalysis. J. Org. Chem. 84, 1677–1686 (2019).
Reiss, H. et al. Cobalt(II)[salen]-catalyzed selective cardio oxidative cross-coupling between electron-rich phenols and 2-naphthols. J. Org. Chem. 84, 7950–7960 (2019).
Röckl, J. L., Schollmeyer, D., Franke, R. & Waldvogel, S. R. Dehydrogenative anodic C−C coupling of phenols bearing electron-withdrawing teams. Angew. Chem. Int. Ed. 59, 315–319 (2020).
Kang, H. et al. Enantioselective vanadium-catalyzed oxidative coupling: growth and mechanistic insights. J. Org. Chem. 83, 14362–14384 (2018).
Libman, A. et al. Artificial and predictive method to unsymmetrical biphenols by iron-catalyzed chelated radical–anion oxidative coupling. J. Am. Chem. Soc. 137, 11453–11460 (2015).
Morimoto, Ok., Sakamoto, Ok., Ohshika, T., Dohi, T. & Kita, Y. Organo-iodine(III)-catalyzed oxidative phenol–arene and phenol–phenol cross-coupling response. Angew. Chem. Int. Ed. 55, 3652–3656 (2016).
Extra, N. Y. & Jeganmohan, M. Oxidative cross-coupling of two completely different phenols: an environment friendly path to unsymmetrical biphenols. Org. Lett. 17, 3042–3045 (2015).
Egami, H. & Katsuki, T. Iron-catalyzed uneven cardio oxidation: oxidative coupling of 2-naphthols. J. Am. Chem. Soc. 131, 6082–6083 (2009).
Hovorka, M., Günterova, J. & Zavada, J. Extremely selective oxidative cross-coupling of substituted 2-naphthols: a handy method to unsymmetrical 1, 1′-binaphthalene-2, 2′-diols. Tetrahedron Lett. 31, 413–416 (1990).
Li, X., Hewgley, J. B., Mulrooney, C. A., Yang, J. & Kozlowski, M. C. Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metallic complexes: environment friendly formation of chiral functionalized BINOL derivatives. J. Org. Chem. 68, 5500–5511 (2003).
Tian, J.-M. et al. Copper-complex-catalyzed uneven cardio oxidative cross-coupling of 2-naphthols: enantioselective synthesis of three,3′-substituted C1-symmetric BINOLs. Angew. Chem. Int. Ed. 58, 11023–11027 (2019).
Bringmann, G. et al. Atroposelective synthesis of axially chiral biaryl compounds. Angew. Chem. Int. Ed. 44, 5384–5427 (2005).
Kočovský, P., Vyskočil, Š. & Smrčina, M. Non-symmetrically substituted 1,1‘-binaphthyls in enantioselective catalysis. Chem. Rev. 103, 3213–3246 (2003).
Kozlowski, M. C., Morgan, B. J. & Linton, E. C. Complete synthesis of chiral biaryl pure merchandise by uneven biaryl coupling. Chem. Soc. Rev. 38, 3193–3207 (2009).
Bringmann, G., Gulder, T., Gulder, T. A. M. & Breuning, M. Atroposelective complete synthesis of axially chiral biaryl pure merchandise. Chem. Rev. 111, 563–639 (2011).
Aldemir, H., Richarz, R. & Gulder, T. A. The biocatalytic repertoire of pure biaryl formation. Angew. Chem. Int. Ed. 53, 8286–8293 (2014).
Mate, D. M. & Alcalde, M. Laccase: a multi-purpose biocatalyst on the forefront of biotechnology. Microb. Biotechnol. 10, 1457–1467 (2017).
Sagui, F. et al. Laccase-catalyzed coupling of catharanthine and vindoline: an environment friendly method to the bisindole alkaloid anhydrovinblastine. Tetrahedron 65, 312–317 (2009).
Obermaier, S., Thiele, W., Fürtges, L. & Müller, M. Enantioselective phenol coupling by laccases within the biosynthesis of fungal dimeric naphthopyrones. Angew. Chem. Int. Ed. 58, 9125–9128 (2019).
Fasan, R. Tuning P450 enzymes as oxidation catalysts. ACS Catal. 2, 647–666 (2012).
Gil Girol, C. et al. Regio‐ and stereoselective oxidative phenol coupling in Aspergillus niger. Angew. Chem. Int. Ed. 51, 9788–9791 (2012).
Mazzaferro, L. S., Huttel, W., Fries, A. & Müller, M. Cytochrome P450-catalyzed regio- and stereoselective phenol coupling of fungal pure merchandise. J. Am. Chem. Soc. 137, 12289–12295 (2015).
Chakrabarty, S., Wang, Y., Perkins, J. C. & Narayan, A. R. H. Scalable biocatalytic C–H oxyfunctionalization reactions. Chem. Soc. Rev. 49, 8137–8155 (2020).
Noji, M., Nakajima, M. & Koga, Ok. A brand new catalytic system for cardio oxidative coupling of 2-naphthol derivatives by means of CuCl-amine complicated: a sensible synthesis of binaphthol derivatives. Tetrahedron Lett. 35, 7983–7984 (1994).
Nakajima, M. Synthesis and software of novel biaryl compounds with axial chirality as catalysts in enantioselective reactions. Yakugaku Zasshi 120, 68–75 (2000).
Langeslay, R. R. et al. Catalytic purposes of vanadium: a mechanistic perspective. Chem. Rev. 119, 2128–2191 (2018).
Shannon, P. et al. Cytoscape: a software program surroundings for built-in fashions of biomolecular interplay networks. Genome Res. 13, 2498–2504 (2003).
Gerlt, J. A. et al. Enzyme Operate Initiative-Enzyme Similarity Software (EFI-EST): an internet instrument for producing protein sequence similarity networks. Biochim. Biophys. Acta 1854, 1019–1037 (2015).
Zallot, R., Oberg, N. O. & Gerlt, J. A. ‘Democratized’ genomic enzymology net instruments for purposeful task. Curr. Opin. Chem. Biol. 47, 77–85 (2018).
Zallot, R., Oberg, N. & Gerlt, J. A. The EFI net useful resource for genomic enzymology instruments: leveraging protein, genome, and metagenome databases to find novel enzymes and metabolic pathways. Biochemistry 58, 4169–4182 (2019).
Funa, N., Funabashi, M., Ohnishi, Y. & Horinouchi, S. Biosynthesis of hexahydroxyperylenequinone melanin by way of oxidative aryl coupling by cytochrome P-450 in Streptomyces griseus. J. Bacteriol. 187, 8149–8155 (2005).
Zhao, B. et al. Binding of two flaviolin substrate molecules, oxidative coupling, and crystal construction of Streptomyces coelicolor A3(2) cytochrome P450 158A2. J. Biol. Chem. 280, 11599–11607 (2005).
Li, S., Podust, L. M. & Sherman, D. H. Engineering and evaluation of a self-sufficient biosynthetic cytochrome P450 PikC fused to the RhFRED reductase area. J. Am. Chem. Soc. 129, 12940–12941 (2007).
[ad_2]