A metal-free iodine-mediated conversion of hydroxamates to esters

References

• Otera, J.; Nishikido, J. Esterification, Methods, Reactions, and Applications, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2010.
   Google Scholar
• Wang, S.-M.; Alharbi, N. S.; Qin, H.-L. One-Pot Synthesis of N-Arylated Amines by HydroaminomethylAtion of 2,5-Dihydrofuran with Aromatic Amines. Synthesis 2019, 51, 1585–3907. DOI: 10.1055/s-0039-1690017.
   Web of Science ®Google Scholar
• Hou, F.; Wang, X.-C.; Quan, Z.-J. Efficient Synthesis of Esters through Oxone-Catalyzed Dehydrogenation of Carboxylic Acids and Alcohols. Org. Biomol. Chem. 2018, 16, 9472–9476. DOI: 10.1039/c8ob02539h.
   PubMed Web of Science ®Google Scholar
• Vandamme, M.; Bouchard, L.; Gilbert, A.; Keita, M.; Paquin, J. F. Direct Esterification of Carboxylic Acids with Perfluorinated Alcohols Mediated by XtalFluor-E. Org. Lett. 2016, 18, 6468–6471. DOI: 10.1021/acs.orglett.6b03365.
   PubMed Web of Science ®Google Scholar
• Gowrisankar, S.; Neumann, H.; Beller, M. General and Selective Palladium-Catalyzed Oxidative Esterification of Alcohols. Angew. Chem. Int. Ed. 2011, 50, 5139–5143. DOI: 10.1002/anie.201008035.
   PubMedGoogle Scholar
• Rout, S. K.; Guin, S.; Ghara, K. K.; Banerjee, A.; Patel, B. K. Copper Catalyzed Oxidative Esterification of Aldehydes with Alkylbenzenes via Cross Dehydrogenative Coupling. Org. Lett. 2012, 14, 3982–3985. DOI: 10.1021/ol301756y.
   PubMed Web of Science ®Google Scholar
• Salome, C.; Kohn, H. Triphenylphosphine Dibromide: A Simple One-Pot Esterification Reagent. Tetrahedron 2009, 65, 456–460. DOI: 10.1016/j.tet.2008.10.062.
   PubMed Web of Science ®Google Scholar
• Chavan, S. P.; Kale, R. R.; Shivasankar, K.; Chandake, S. I.; Benjamin, S. B. A Simple and Efficient Method for Transesterification of β-Ketoesters Catalysed by Iodine. Synthesis 2003, 17, 2695–2698. DOI: 10.1055/s-2003-42433.
   Web of Science ®Google Scholar
• Liu, C.; Tang, S.; Zheng, L.; Liu, D.; Zhang, H.; Lei, A. Covalently Bound Benzyl Ligand Promotes Selective Palladium-Catalyzed Oxidative Esterification of Aldehydes with Alcohols. Angew. Chem. Int. Ed. 2012, 51, 5662–5666. DOI: 10.1002/anie.201201960.
   PubMed Web of Science ®Google Scholar
• Twibanire, J. K.; Grindley, T. B. Efficient and Controllably Selective Preparation of Esters Using Uronium-Based Coupling Agents. Org. Lett. 2011, 13, 2988–2991. DOI: 10.1021/ol201005s.
   PubMed Web of Science ®Google Scholar
• Petersen, T. B.; Khan, R.; Olofsson, B. Metal-Free Synthesis of Aryl Esters from Carboxylic Acids and Diaryliodonium Salts. Org. Lett. 2011, 13, 3462–3465. DOI: 10.1021/ol2012082.
   PubMed Web of Science ®Google Scholar
• Crawford, R. J.; Raap, R. The Synthesis and Reactions of N,N'-Dicarbalkoxy-N,N'-Dialkoxyhydrazines and Some Observations on Carbalkoxylium Ions. J. Org. Chem. 1963, 28, 2419–2424. DOI: 10.1021/jo01044a066.
   Web of Science ®Google Scholar
• De Almeida, M. V.; Barton, D. H. R.; Bytheway, I.; Ferreira, J. A.; Hall, M. B.; Liu, W.; Taylor, D. K.; Thomson, L. Preparation and Thermal Decomposition of N,N'-Diacyl-N,N'-Dialkoxyhydrazines: Synthetic Applications and Mechanistic Insights. J. Am. Chem. Soc. 1995, 117, 4870–4874. DOI: 10.1021/ja00122a018.
   Web of Science ®Google Scholar
• Cooley, J. H.; Mosher, M. W.; Khan, M. A. Preparation and Reactions of N,N'-Diacyl-N,N'-Dialkoxyhydrazines. J. Am. Chem. Soc. 1968, 90, 1867–1871. DOI: 10.1021/ja01009a032.
   Web of Science ®Google Scholar
• Glover, S. A.; Mo, G.; Rauk, A. HERON Rearrangement of N,N′-Diacyl-N,N′-Dialkoxyhydrazines – A Theoretical and Experimental Study. Tetrahedron 1999, 5, 3413–3426. DOI: 10.1016/S0040-4020(98)01151-X.
   Google Scholar
• Duan, X.; Yang, K.; Tian, S.; Ma, J.; Li, Y.; Zou, J.; Zhang, D.; Cui, H. Copper-Mediated Oxidative Homocoupling and Rearrangement of N-Alkoxyamides: An Efficient Method for the Preparation of Aromatic Esters. Tetrahedron Lett. 2015, 56, 4634–4637. DOI: 10.1016/j.tetlet.2015.06.023.
   Web of Science ®Google Scholar
• Zhou, L.; Yi, H.; Zhu, L.; Qi, X.; Jiang, H.; Liu, C.; Feng, Y.; Lan, Y.; Lei, A. Tuning the Reactivity of Radical through a Triplet Diradical Cu(II) Intermediate in Radical Oxidative Cross-Coupling. Sci. Rep. 2015, 5, 15934–15943. DOI: 10.1038/srep15934.
   PubMed Web of Science ®Google Scholar
• Zhou, L.; Tang, S.; Qi, X.; Lin, C.; Liu, K.; Liu, C.; Lan, Y.; Lei, A. Transition-Metal-Assisted Radical/Radical Cross-Coupling: A New Strategy to the Oxidative C(sp3)–H/N–H Cross-Coupling. Org. Lett. 2014, 16, 3404–3407. DOI: 10.1021/ol501485f. .
   PubMed Web of Science ®Google Scholar
• Duan, X.; Duan, X.; Yang, K.; Wang, Z.; Zhang, L.; Tong, Y.; Liu, H.; Du, K.; Tang, R. PhI(OAc)2/I2-Mediated Oxidative Homocoupling of N-Alkoxyamides: An Approach to Esters. Chin. J. Org. Chem. 2015, 35, 2552–2558. DOI: 10.6023/cjoc201506024.
   Web of Science ®Google Scholar
• Zhang, N.; Yang, R.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Direct Conversion of N-Alkoxyamides to Carboxylic Esters through Tandem NBS-Mediated Oxidative Homocoupling and Thermal Denitrogenation. J. Org. Chem. 2013, 78, 8705–8711. DOI: 10.1021/jo401435v.
   PubMed Web of Science ®Google Scholar
• Glover, S. A.; Mo, G. J. Hindered Ester Formation by SN2 Azidation of N-Acetoxy-N-Alkoxyamides and N-Alkoxy-N-Chloroamides—Novel Application of HERON Rearrangements. J. Chem. Soc., Perkin Trans.1. 2002, 2, 1728–1739. DOI: 10.1039/B111250N.
   Google Scholar
• Subramanian, K.; Yedage, S. L.; Bhanage, B. M. An Electrochemical Method for Carboxylic Ester Synthesis from N-Alkoxyamides. J. Org. Chem. 2017, 82, 10025–10032. DOI: 10.1021/acs.joc.7b01473.
   PubMed Web of Science ®Google Scholar
• Mahato, K.; Arora, N.; Ray Bagdi, P.; Gattu, R.; Ghosh, S. S.; Khan, A. T. An Oxidative Cross-Coupling Reaction of 4-Hydroxydithiocoumarin and Amines/Thiols Using a Combination of I2 and TBHP: Access to Lead Molecules for Biomedical Applications. Chem. Commun. 2018, 54, 1513–1516. DOI: 10.1039/C7CC08502H.
   PubMed Web of Science ®Google Scholar
• Finkbeiner, P.; Nachtsheim, B. J. Iodine in Modern Oxidation Catalysis. Synthesis 2013, 45, 979–999. DOI: 10.1055/s-0032-1318330.
   Web of Science ®Google Scholar
• Jereb, M.; Vražič, D.; Zupan, M. Iodine-Catalyzed Transformation of Molecules Containing Oxygen Functional Groups. Tetrahedron 2011, 67, 1355. DOI: 10.1016/j.tet.2010.11.086.
   Web of Science ®Google Scholar
• Aggarwal, T.; Kumar, S.; Verma, A. K. Iodine-Mediated Synthesis of Heterocycles via Electrophilic Cyclization of Alkynes. Org. Biomol. Chem. 2016, 14, 7639–7653. DOI: 10.1039/C6OB01054G.
   PubMed Web of Science ®Google Scholar
• Parvatkar, P. T.; Parameswaran, P. S.; Tilve, S. G. Recent Developments in the Synthesis of Five- and Six-Membered Heterocycles Using Molecular Iodine. Chemistry 2012, 18, 5460–5489. DOI: 10.1002/chem.201100324.
   PubMed Web of Science ®Google Scholar
• Kandimalla, S. R.; Parvathaneni, S. P.; Sabitha, G.; Subba Reddy, B. V. Recent Advances in Intramolecular Metal‐Free Oxidative C–H Bond Aminations Using Hypervalent Iodine(III) Reagents. Eur. J. Org. Chem. 2019, 2019, 1687. DOI: 10.1002/ejoc.201801469.
   Web of Science ®Google Scholar
• Nanjo, T.; Kato, N.; Takemoto, Y. Oxidative Decarboxylation Enables Chemoselective, Racemization-Free Esterification: Coupling of α-Ketoacids and Alcohols Mediated by Hypervalent Iodine(III). Org. Lett. 2018, 20, 5766–5759. DOI: 10.1021/acs.orglett.8b02466.
   PubMed Web of Science ®Google Scholar
• Kumar, S.; Patel, M.; Saunthwal, R. K.; Verma, A. K. Chemoselective Oxidative Esterification and Iodocyclization of Hydroxyalkynyl Aldehydes. Asian J. Org. Chem. 2017, 6, 1893–1902. DOI: 10.1002/ajoc.201700375.
   Web of Science ®Google Scholar
• Maejima, S.; Yamaguchi, E.; Itoh, A. Intermolecular Tandem Addition/Esterification Reaction of Alkenes with Malonates Leading to γ-Lactones Mediated by Molecular Iodine under Visible Light Irradiation. Adv. Synth. Catal. 2017, 359, 3883–3887. DOI: 10.1002/adsc.201701424.
   Web of Science ®Google Scholar
• Carle, M. S.; Shimokura, G. K.; Murphy, G. K. Iodobenzene Dichloride in the Esterification and Amidation of Carboxylic Acids: In-Situ Synthesis of Ph 3 PCl 2. Eur. J. Org. Chem. 2016, 2016, 3930–3933. DOI: 10.1002/ejoc.201600714.
   Web of Science ®Google Scholar
• Pathak, G.; Das, D.; Rokhum, L. A Microwave-Assisted Highly Practical Chemoselective Esterification and Amidation of Carboxylic Acids. RSC Adv. 2016, 6, 93729–93740. DOI: 10.1039/C6RA22558F.
   Web of Science ®Google Scholar
• Mamidi, N.; Manna, D. Zn(OTf)2-Promoted Chemoselective Esterification of Hydroxyl Group Bearing Carboxylic Acids. J. Org. Chem. 2013, 78, 2386–2389. DOI: 10.1021/jo302502r.
   PubMed Web of Science ®Google Scholar
• Ghosh, S.; Chattopadhyay, S. K. Metal‐Free Synthesis of 4‐Aryl‐2‐Quinolone Derivatives by Iodine‐Mediated Intramolecular C−H Amidation. Adv. Synth. Catal. 2019, 361, 4727–4738. DOI: 10.1002/adsc.201900530.
   Web of Science ®Google Scholar
• Chattopadhyay, S. K.; Ghosh, S.; Sil, S. Cross Metathesis-Mediated Synthesis of Hydroxamic Acid Derivatives. Beilstein J. Org. Chem. 2018, 14, 3070–3075. DOI: 10.3762/bjoc.14.285.
   PubMed Web of Science ®Google Scholar
• Chattopadhyay, S. K.; Ghosh, S.; Sarkar, S.; Bhadra, K. α,ß-Didehydrosuberoylanilide Hydroxamic Acid (DDSAHA) as Precursor and Possible Analogue of the Anticancer Drug SAHA. Beilstein J. Org. Chem. 2019, 15, 2524–2533. DOI: 10.3762/bjoc.15.245.
   PubMed Web of Science ®Google Scholar
• Buccigross, J. M.; Glover, S. A. Molecular Orbital Studies of Novel N to C Migrations in N,N-Bisheteroatom-Substituted Amides—HERON Rearrangements. J. Chem. Soc. Perkin Trans. 2. 1995, 3, 595–603. DOI: 10.1039/P29950000595.
   Google Scholar