References
- Petrone, D. A.; Ye, J.; Lautens, M. Modern Transition-Metal-Catalyzed Carbon-Halogen Bond Formation. Chem. Rev. 2016, 116, 8003–8104. DOI: https://doi.org/10.1021/acs.chemrev.6b00089.
- Nelson, J. D. In Practical Synthetic Organic Chemistry: Reactions, Principles and Techniques. Caron, S. Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2011.
- (a) Kim, J. H.; Ko, Y. O.; Bouffard, J. S.; Lee, G. Advances in Tandem Reactions with Organozinc Reagents. Chem. Soc. Rev. 2015, 44, 2489–2507. DOI: https://doi.org/10.1039/c4cs00430b. (b) Sun, C. L.; Shi, Z. J. Transition-Metal-Free Coupling Reactions. Chem. Rev. 2014, 114, 9219–9280. DOI: https://doi.org/10.1021/cr400274j.
- (a) Muller, K.; Faeh, C.; Diederich, F. Fluorine in Pharmaceuticals: Looking Beyond Intuition. Science 2007, 317, 1881–1886. DOI: https://doi.org/10.1126/science.1131943. (b) Hernandes, M.; Cavalcanti, S. M.; Moreira, D. R.; de Azevedo, W.; Jr.; Leite, A. C. Halogen Atoms in the Modern Medicinal Chemistry: Hints for the Drug Design. Curr. Drug Targets 2010, 11, 303–314. DOI: https://doi.org/10.2174/138945010790711996. (c) Wilcken, R.; Zimmermann, M. O.; Lange, A.; Joerger, A. C.; Boeckler, F. M. Principles and Applications of Halogen Bonding in Medicinal Chemistry and Chemical Biology. J. Med. Chem. 2013, 56, 1363–1388. DOI: https://doi.org/10.1021/jm3012068.
- (a) Davies, J.; Caseley, J. C. Herbicide Safeners: A Review. Pestic. Sci. 1999, 55, 1043–1058. DOI: https://doi.org/10.1002/(SICI)1096-9063(199911)55:11<1043::AID-PS60>3.0.CO;2-L. (b) Jeschke, P. The Unique Role of Halogen Substituents in the Design of Modern Agrochemicals. Pest Manag. Sci. 2010, 66, 10–27. DOI: https://doi.org/10.1002/ps.1829.
- (a) Amanchukwu, C. V.; Harding, J. R.; Shao-Horn, Y.; Hammond, P. T. Understanding the Chemical Stability of Polymers for Lithium–Air Batteries. Chem. Mater. 2015, 27, 550–561. DOI: https://doi.org/10.1021/cm5040003. (b) Tang, M. L.; Bao, Z. Halogenated Materials as Organic Semiconductors. Chem. Mater. 2011, 23, 446–455. DOI: https://doi.org/10.1021/cm102182x.
- (a) Liu, W.; Groves, J. T. Manganese Porphyrins Catalyze Selective C-H Bond Halogenations. J. Am. Chem. Soc. 2010, 132, 12847–12849. DOI: https://doi.org/10.1021/ja105548x. (b) McCallum, T.; Slavko, E.; Morin, M.; Barriault, L. Light-Mediated Deoxygenation of Alcohols with a Dimeric Gold Catalyst. Eur. J. Org. Chem. 2015, 2015, 81–85. DOI: https://doi.org/10.1002/ejoc.201403351. (c) Podgorsek, A.; Zupan, M.; Iskra, J. Oxidative Halogenation with “Green” Oxidants: Oxygen and Hydrogen Peroxide. Angew. Chem. Int. Ed. 2009, 48, 8424–8450. DOI: https://doi.org/10.1002/anie.200901223. (d) Mohite, A. R.; Phatake, R. S.; Dubey, P.; Agbaria, M.; Shames, A. I.; Lemcoff, N. G.; Reany, O. Thiourea-Mediated Halogenation of Alcohols. J. Org. Chem. 2020, 85, 12901–12911. DOI: https://doi.org/10.1021/acs.joc.0c01431.
- (a) Campbell, M. G.; Ritter, T. Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis. Chem. Rev. 2015, 115, 612–633. DOI: https://doi.org/10.1021/cr500366b. (b) Huy, P. H.; Motsch, S.; Kappler, S. M. Formamides as Lewis Base Catalysts in SN Reactions-Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers. Angew. Chem. Int. Ed. 2016, 55, 10145–10149. DOI: https://doi.org/10.1002/anie.201604921. (c) Munyemana, F.; George, I.; Devos, A.; Colens, A.; Badarau, E.; Frisque-Hesbain, A. M.; Loudet, A.; Differding, E.; Damien, J. M.; Remion, J.; et al. A Mild Method for the Replacement of a Hydroxyl Group by Halogen. 1. Scope and Chemoselectivity. Tetrahedron 2016, 72, 420–430. DOI: https://doi.org/10.1016/j.tet.2015.11.060.
- (a) Chen, J.; Lin, J.-H.; Xiao, J. C. Halogenation through Deoxygenation of Alcohols and Aldehydes. Org. Lett. 2018, 20, 3061–3064. DOI: https://doi.org/10.1021/acs.orglett.8b01058. (b) Ren, R. X.; Wu, J. X. Mild Conversion of Alcohols to Alkyl Halides Using Halide-Based Ionic Liquids at Room Temperature. Org. Lett. 2001, 3, 3727–3728. DOI: https://doi.org/10.1021/ol016672r. (c) Liang, S.; Kumon, T.; Angnes, R. A.; Sanchez, M.; Xu, B.; Hammond, G. B. Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation. Org. Lett. 2019, 21, 3848–3854. DOI: https://doi.org/10.1021/acs.orglett.9b01337. (d) McCallum, T.; Slavko, E.; Morin, M.; Barriault, L. Light-Mediated Deoxygenation of Alcohols with a Dimeric Gold Catalyst. Eur. J. Org. Chem. 2015, 2015, 81–85. DOI: https://doi.org/10.1002/ejoc.201403351. (e) Lee, C. H.; Lee, S. M.; Min, B. H.; Kim, D. S.; Jun, C. H. Ferric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids Using α,α-Dichlorodiphenylmethane. Org. Lett. 2018, 20, 2468–2471. 20, DOI: https://doi.org/10.1021/acs.orglett.8b00831. (f) Moriya, T.; Yoneda, S.; Kawana, K.; Ikeda, R.; Konakahara, T.; Sakai, N. Indium-Catalyzed Reductive Bromination of Carboxylic Acids Leading to Alkyl Bromides. Org. Lett. 2012, 14, 4842–4845. DOI: https://doi.org/10.1021/ol302168q. (g) Tan, X.; Song, T.; Wang, Z.; Chen, H.; Cui, L.; Li, C. Silver-Catalyzed Decarboxylative Bromination of Aliphatic Carboxylic Acids. Org. Lett. 2017, 19, 1634–1637. DOI: https://doi.org/10.1021/acs.orglett.7b00439. (h) Longwitz, L.; Jopp, S.; Werner, T. Organocatalytic Chlorination of Alcohols by P(III)/P(V) Redox Cycling. J. Org. Chem. 2019, 84, 7863–7870. DOI: https://doi.org/10.1021/acs.joc.9b00741.
- (a) Smeaton, E.; Smith, M. H.; White, M. J. Science of Synthesis, Reagents: Halogenation; Georg Thieme Verlag KG: Stuttgart, NY, 2013. (b) Weiss, R. G.; Snyder, E. I. J. Chem. Soc. Chem. Commun. 1968, 21, 1358–1359. (c) Weiss, R. G.; Snyder, E. I. Stereochemistry of Displacement Reactions at the Neopentyl Carbon. Further Observations on the Triphenylphosphine-Polyhalomethane-Alcohol Reaction. J. Org. Chem. 1971, 36, 403–406. DOI: https://doi.org/10.1021/jo00802a009. (d) Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; New York: John Wiley & Sons, 1999.
- Pouliot, M. F.; Mahe, O.; Hamel, J. D.; Desroches, J.; Paquin, J. F. Halogenation of Primary Alcohols Using a Tetraethylammonium Halide/[Et2NSF2]BF4 Combination. Org. Lett. 2012, 14, 5428–5431. DOI: https://doi.org/10.1021/ol302496q.
- Luca, L. D.; Giacomelli, G.; Porcheddu, A. An Efficient Route to Alkyl Chlorides from Alcohols Using the Complex TCT/DMF. Org. Lett. 2002, 4, 553–555. DOI: https://doi.org/10.1021/ol017168p.
- Mohanazadeh, F.; Zolfigol, M. A.; Sedrpoushan, A.; Veisi, H. Synthesis of Silica Bromide as Heterogeneous Reagent and Its Application to Conversion of Alcohols to Alkyl Bromides. Loc. 2012, 9, 598–603. DOI: https://doi.org/10.2174/157017812802850285.
- Fujisawa, T.; Iida, S.; Sato, T. A Convenient Method for the Transformation of Alcohols to Alkyl Chlorides Using N, N -Diphenylchlorophenylmethyleniminium Chloride. Chem. Lett. 1984, 13, 1173–1174. DOI: https://doi.org/10.1246/cl.1984.1173.
- Ajvazi, N.; Stavber, S. Direct Halogenation of Alcohols with Halosilanes under Catalyst- and Organic Solvent-Free Reaction Conditions. Tetrahedron Lett. 2016, 57, 2430–2433. DOI: https://doi.org/10.1016/j.tetlet.2016.04.083.
- Das, P. J.; Das, J.; Das, D. An Efficient Conversion of Alcohols to Alkyl Bromides Using Pyridinium Based Ionic Liquids: A Green Alternative to Appel Reaction. Asian J. Chem. 2018, 30, 651–654. DOI: https://doi.org/10.14233/ajchem.2018.21086.
- Mukaiyama, T.; Shoda, S-i.; Watanabe, Y. A New Synthetic Method for the Transformation of Alcohols to Alkyl Chlorides Using 2-Chlorobenzoxazolium Salt. Chem. Lett. 1977, 6, 383–386. DOI: https://doi.org/10.1246/cl.1977.383.
- Iranpoor, N.; Firouzabadi, H.; Jamalian, A.; Kazemi, F. Silicaphosphine (Silphos): a Filterable Reagent for the Conversion of Alcohols and Thiols to Alkyl Bromides and Iodides. Tetrahedron 2005, 61, 5699–5704. DOI: https://doi.org/10.1016/j.tet.2005.01.115.
- (a) Appel, R. Tertiary Phosphane/Tetrachloromethane, a Versatile Reagent for Chlorination, Dehydration, and P—N Linkage. Angew. Chem. Int. Ed. 1975, 14, 801–811. DOI: https://doi.org/10.1002/anie.197508011. (b) Liu, Y.; Xu, Y.; Jung, S. H.; Chae, J. A Facile and Green Protocol for Nucleophilic Substitution Reactions of Sulfonate Esters by Recyclable Ionic Liquids [Bmim][X]. Synlett 2012, 23, 2692–2698. DOI: https://doi.org/10.1055/s-0032-1317473. (c) Desmaris, L.; Percina, N.; Cottier, L.; Sinou, D. Conversion of Alcohols to Bromides Using a Fluorous Phosphine. Tetrahedron Lett. 2003, 44, 7589–7591. DOI: https://doi.org/10.1016/j.tetlet.2003.08.064.
- (a) Nicolaou, K. C.; Harter, M. W.; Gunzner, J. L.; Nadin, A. The Wittig and Related Reactions in Natural Product Synthesis. Liebigs Ann/Recl. 1997, 1997, 1283–1301. DOI: https://doi.org/10.1002/jlac.199719970704. (b) Vedejs, E.; Peterson, M. J. Adv. Carbanion Chem. 1996, 2, 1. (c) Maryanoff, B. E.; Reitz, A. B. The Wittig Olefination Reaction and Modifications Involving Phosphoryl-Stabilized Carbanions. Stereochemistry, Mechanism, and Selected Synthetic Aspects. Chem. Rev. 1989, 89, 863–927. DOI: https://doi.org/10.1021/cr00094a007. (d) Hoffmann, M.; Deshmukh, S.; Werner, T. Org. Lett 2015, 17, 3078–3081. (e) Lao, Z. P.; Toy, H. Catalytic Wittig and aza-Wittig Reactions. Beilstein J. Org. Chem. 2016, 12, 2577–2587. DOI: https://doi.org/10.3762/bjoc.12.253.
- (a) Swamy, K. C. K.; Kumar, N. N. B.; Balaraman, K. E.; Kumar, K. V. P. P. Mitsunobu and Related Reactions: Advances and Applications. Chem. Rev. 2009, 109, 2551–2651. DOI: https://doi.org/10.1021/cr800278z. (b) Buonomo, J. A.; Aldrich, C. C. Mitsunobu Reactions Catalytic in Phosphine and a Fully Catalytic System. Angew. Chem. Int. Ed. 2015, 54, 13041–13044. DOI: https://doi.org/10.1002/anie.201506263. (c) Hirose, D.; Gazvoda, M.; Kosmrlj, J.; Taniguchi, T. The “Fully Catalytic System” in Mitsunobu Reaction Has Not Been Realized Yet. Org. Lett. 2016, 18, 4036–4039. DOI: https://doi.org/10.1021/acs.orglett.6b01894.
- (a) Kosal, A. D.; Wilson, E. E.; Ashfeld, B. L. Phosphine-Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides. Angew. Chem. Int. Ed. 2012, 51, 12036–12040. DOI: https://doi.org/10.1002/anie.201206533. (b) Lenstra, D. C.; Lenting, P. E.; Mecinovic, J. Sustainable Organophosphorus-Catalysed Staudinger Reduction. Green Chem. 2018, 20, 4418–4422. DOI: https://doi.org/10.1039/C8GC02136H.
- (a) Nagle, A. S.; Salvatore, R. N.; Chong, B. D.; Jung, K. W. Efficient Synthesis of β-Amino Bromides. Tetrahedron Lett. 2000, 41, 3011–3014. DOI: https://doi.org/10.1016/S0040-4039(00)00330-0. (b) Subiptha Kumar, M.; Panda, G. RSC Adv. 2013, 3, 18332–18338. (c) Mirilashvili, S.; Rubinstein, N. C.; Albeck, A. Optically Active N- and C-Terminal Building Blocks for the Synthesis of Peptidyl Olefin Peptidomimetics. Eur. J. Org. Chem. 2010, 2010, 4671–4686. DOI: https://doi.org/10.1002/ejoc.201000539. (d) Higashiura, K.; Morino, H.; Matsuura, H.; Toyomaki, Y.; Ienaga, K. Syntheses and Properties of Optically Active 2-Substituted Taurines. J. Chem. Soc. 1989, 1, 1479–1481. DOI: https://doi.org/10.1039/p19890001479.
- Chong, H. S.; Song, H. A.; Dadwal, M.; Sun, X.; Sin, I.; Chen, Y. Efficient Synthesis of Functionalized Aziridinium Salts. J. Org. Chem. 2010, 75, 219–221. DOI: https://doi.org/10.1021/jo901893n.