Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols

Hatch, Chad E.; Martin, Maxwell I.; Gilmartin, Philip H.; Xiong, Lu; Beam, Danielle J.; Yap, Glenn P.  A.; Von Bargen, Matthew J.; Rosenthal, Joel; Chain, William J.

doi:10.1021/acs.orglett.1c03860

Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols

Journal Article · 11 February 2022 · Organic Letters

DOI:https://doi.org/10.1021/acs.orglett.1c03860· OSTI ID:1978214

Hatch, Chad E. ^[1]; Martin, Maxwell I. ^[1]; ^[1]; Xiong, Lu ^[1]; Beam, Danielle J. ^[1]; ^[1]; Von Bargen, Matthew J. ^[1]; ^[1]; ^[1]

Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States

Not provided.

Research Organization:: Univ. of California, Los Angeles, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0001234

OSTI ID:: 1978214

Journal Information:: Organic Letters, Vol. 24, Issue 7; ISSN 1523-7060

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

References (87)

13. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols Bowden, Kenneth; Heilbron, I. M.; Jones, E. R. H. Journal of the Chemical Society (Resumed) https://doi.org/10.1039/jr9460000039	journal	January 1946
Aldehydes from Primary Alcohols by Oxidation with Chromium Trioxide: Heptanal No authors listed Organic Syntheses, Vol. 52, p. 5 https://doi.org/10.15227/orgsyn.052.0005	journal	January 1972
Mono‐Gold(I)‐Catalyzed Enantioselective Intermolecular Reaction of Ynones with Styrenes: Tandem Diels–Alder and Ene Sequence Nanko, Masaki; Inaba, Yuya; Sekine, Keisuke Helvetica Chimica Acta, Vol. 104, Issue 2 https://doi.org/10.1002/hlca.202000198	journal	January 2021
Laccase‐mediated Oxidations of Propargylic Alcohols. Application in the Deracemization of 1‐arylprop‐2‐yn‐1‐ols in Combination with Alcohol Dehydrogenases González‐Granda, Sergio; Méndez‐Sánchez, Daniel; Lavandera, Iván ChemCatChem, Vol. 12, Issue 2 https://doi.org/10.1002/cctc.201901543	journal	October 2019
Unified Approach to Furan Natural Products via Phosphine‐Palladium Catalysis Chen, Violet Yijang; Kwon, Ohyun Angewandte Chemie International Edition, Vol. 60, Issue 16 https://doi.org/10.1002/anie.202015232	journal	March 2021
The Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Ynones with Azomethine Ylides Shi, Feng; Luo, Shi-Wei; Tao, Zhong-Lin Organic Letters, Vol. 13, Issue 17 https://doi.org/10.1021/ol201898x	journal	August 2011
Palladacycle-Catalyzed Reaction of Bicyclic Alkenes with Terminal Ynones: Regiospecific Synthesis of Polysubstituted Furans Ge, Guang-Cun; Mo, Dong-Liang; Ding, Chang-Hua Organic Letters, Vol. 14, Issue 22 https://doi.org/10.1021/ol302586m	journal	November 2012
2-Bromoanthraquinone as a highly efficient photocatalyst for the oxidation of sec -aromatic alcohols: experimental and DFT study Liao, Shengfu; Liu, Jianguo; Yan, Long RSC Advances, Vol. 10, Issue 61 https://doi.org/10.1039/D0RA06414A	journal	January 2020
Total Synthesis of (−)-Oxycodone via Anodic Aryl–Aryl Coupling Lipp, Alexander; Selt, Maximilian; Ferenc, Dorota Organic Letters, Vol. 21, Issue 6 https://doi.org/10.1021/acs.orglett.9b00419	journal	February 2019
11-Step Total Synthesis of Teleocidins B-1–B-4 Nakamura, Hugh; Yasui, Kosuke; Kanda, Yuzuru Journal of the American Chemical Society, Vol. 141, Issue 4 https://doi.org/10.1021/jacs.8b13697	journal	December 2018
Recent Advances in Organic Electrochemical Synthesis and Application of Hypervalent Iodine Reagents Zhang, Huaiyuan; Tang, Rongping; Shi, Xingli Chinese Journal of Organic Chemistry, Vol. 39, Issue 7 https://doi.org/10.6023/cjoc201902006	journal	January 2019
Total synthesis of biseokeaniamides A–C and late-stage electrochemically-enabled peptide analogue synthesis Lin, Yutong; Malins, Lara R. Chemical Science, Vol. 11, Issue 39 https://doi.org/10.1039/D0SC03701J	journal	January 2020
Electrochemical Total Synthesis of Pyrrolophenanthridone Alkaloids: Controlling the Anodically Initiated Electron Transfer Process Okamoto, Kazuhiro; Chiba, Kazuhiro Organic Letters, Vol. 22, Issue 9 https://doi.org/10.1021/acs.orglett.0c01082	journal	April 2020
Total synthesis of Myc-IV(C16:0, S) via automated electrochemical assembly Yano, Kumpei; Itoh, Toshiyuki; Nokami, Toshiki Carbohydrate Research, Vol. 492 https://doi.org/10.1016/j.carres.2020.108018	journal	June 2020
Asymmetric Total Syntheses of 8,9‐Seco‐ ent ‐kaurane Diterpenoids Enabled by an Electrochemical ODI‐[5+2] Cascade Wang, Bingnan; Liu, Zhaobo; Tong, Zhenzhong Angewandte Chemie International Edition, Vol. 60, Issue 27 https://doi.org/10.1002/anie.202104410	journal	June 2021
Total Synthesis of Dixiamycin B by Electrochemical Oxidation Rosen, Brandon R.; Werner, Erik W.; O’Brien, Alexander G. Journal of the American Chemical Society, Vol. 136, Issue 15 https://doi.org/10.1021/ja5013323	journal	April 2014
Scalable and sustainable electrochemical allylic C–H oxidation Horn, Evan J.; Rosen, Brandon R.; Chen, Yong Nature, Vol. 533, Issue 7601 https://doi.org/10.1038/nature17431	journal	April 2016
Scalable, Electrochemical Oxidation of Unactivated C–H Bonds Kawamata, Yu; Yan, Ming; Liu, Zhiqing Journal of the American Chemical Society, Vol. 139, Issue 22 https://doi.org/10.1021/jacs.7b03539	journal	May 2017
Electrochemically Enabled, Nickel-Catalyzed Amination Li, Chao; Kawamata, Yu; Nakamura, Hugh Angewandte Chemie International Edition, Vol. 56, Issue 42 https://doi.org/10.1002/anie.201707906	journal	September 2017
Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance Yan, Ming; Kawamata, Yu; Baran, Phil S. Chemical Reviews, Vol. 117, Issue 21 https://doi.org/10.1021/acs.chemrev.7b00397	journal	October 2017
Synthetic Organic Electrochemistry: Calling All Engineers Yan, Ming; Kawamata, Yu; Baran, Phil S. Angewandte Chemie International Edition, Vol. 57, Issue 16 https://doi.org/10.1002/anie.201707584	journal	November 2017
Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications Kawamata, Yu; Vantourout, Julien C.; Hickey, David P. Journal of the American Chemical Society, Vol. 141, Issue 15 https://doi.org/10.1021/jacs.9b01886	journal	March 2019
Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry Peters, Byron K.; Rodriguez, Kevin X.; Reisberg, Solomon H. Science, Vol. 363, Issue 6429 https://doi.org/10.1126/science.aav5606	journal	February 2019
Hindered dialkyl ether synthesis with electrogenerated carbocations Xiang, Jinbao; Shang, Ming; Kawamata, Yu Nature, Vol. 573, Issue 7774 https://doi.org/10.1038/s41586-019-1539-y	journal	September 2019
Electrochemical Cyclobutane Synthesis in Flow: Scale-Up of a Promising Melt-Castable Energetic Intermediate Chen, Longrui; Barton, Lisa M.; Vantourout, Julien C. Organic Process Research & Development, Vol. 25, Issue 12 https://doi.org/10.1021/acs.oprd.0c00270	journal	July 2020
Electroreductive Olefin–Ketone Coupling Hu, Pengfei; Peters, Byron K.; Malapit, Christian A. Journal of the American Chemical Society, Vol. 142, Issue 50 https://doi.org/10.1021/jacs.0c11214	journal	December 2020
Electrochemical borylation of carboxylic acids Barton, Lisa M.; Chen, Longrui; Blackmond, Donna G. Proceedings of the National Academy of Sciences, Vol. 118, Issue 34 https://doi.org/10.1073/pnas.2109408118	journal	August 2021
Electrochemical Nozaki–Hiyama–Kishi Coupling: Scope, Applications, and Mechanism Gao, Yang; Hill, David E.; Hao, Wei Journal of the American Chemical Society, Vol. 143, Issue 25 https://doi.org/10.1021/jacs.1c03007	journal	June 2021
Electrochemically driven desaturation of carbonyl compounds Gnaim, Samer; Takahira, Yusuke; Wilke, Henrik R. Nature Chemistry, Vol. 13, Issue 4 https://doi.org/10.1038/s41557-021-00640-2	journal	March 2021
N -Ammonium Ylide Mediators for Electrochemical C–H Oxidation Saito, Masato; Kawamata, Yu; Meanwell, Michael Journal of the American Chemical Society, Vol. 143, Issue 20 https://doi.org/10.1021/jacs.1c03780	journal	May 2021
Chemoselective, Scalable Nickel‐Electrocatalytic O ‐Arylation of Alcohols Zhang, Hai‐Jun; Chen, Longrui; Oderinde, Martins S. Angewandte Chemie International Edition, Vol. 60, Issue 38 https://doi.org/10.1002/anie.202107820	journal	August 2021
Electrochemical Aminoxyl-Mediated α-Cyanation of Secondary Piperidines for Pharmaceutical Building Block Diversification Lennox, Alastair J. J.; Goes, Shannon L.; Webster, Matthew P. Journal of the American Chemical Society, Vol. 140, Issue 36 https://doi.org/10.1021/jacs.8b08145	journal	August 2018
Tetramethylpiperidine N -Oxyl (TEMPO), Phthalimide N -Oxyl (PINO), and Related N -Oxyl Species: Electrochemical Properties and Their Use in Electrocatalytic Reactions Nutting, Jordan E.; Rafiee, Mohammad; Stahl, Shannon S. Chemical Reviews, Vol. 118, Issue 9 https://doi.org/10.1021/acs.chemrev.7b00763	journal	April 2018
Electrochemical Oxidation of Alcohols and Aldehydes to Carboxylic Acids Catalyzed by 4-Acetamido-TEMPO: An Alternative to “Anelli” and “Pinnick” Oxidations Rafiee, Mohammad; Konz, Zachary M.; Graaf, Matthew D. ACS Catalysis, Vol. 8, Issue 7 https://doi.org/10.1021/acscatal.8b01640	journal	May 2018
N -Hydroxyphthalimide-Mediated Electrochemical Iodination of Methylarenes and Comparison to Electron-Transfer-Initiated C–H Functionalization Rafiee, Mohammad; Wang, Fei; Hruszkewycz, Damian P. Journal of the American Chemical Society, Vol. 140, Issue 1 https://doi.org/10.1021/jacs.7b09744	journal	December 2017
Electrochemical Functional‐Group‐Tolerant Shono‐type Oxidation of Cyclic Carbamates Enabled by Aminoxyl Mediators Wang, Fei; Rafiee, Mohammad; Stahl, Shannon S. Angewandte Chemie International Edition, Vol. 57, Issue 22 https://doi.org/10.1002/anie.201803539	journal	May 2018
Electrochemical Aminoxyl-Mediated Oxidation of Primary Alcohols in Lignin to Carboxylic Acids: Polymer Modification and Depolymerization Rafiee, Mohammad; Alherech, Manar; Karlen, Steven D. Journal of the American Chemical Society, Vol. 141, Issue 38 https://doi.org/10.1021/jacs.9b07243	journal	September 2019
Merging Photochemistry with Electrochemistry: Functional-Group Tolerant Electrochemical Amination of C(sp ³ )−H Bonds Wang, Fei; Stahl, Shannon S. Angewandte Chemie International Edition, Vol. 58, Issue 19 https://doi.org/10.1002/anie.201813960	journal	March 2019
Mediated Fuel Cells: Soluble Redox Mediators and Their Applications to Electrochemical Reduction of O ₂ and Oxidation of H ₂ , Alcohols, Biomass, and Complex Fuels Anson, Colin W.; Stahl, Shannon S. Chemical Reviews, Vol. 120, Issue 8 https://doi.org/10.1021/acs.chemrev.9b00717	journal	March 2020
Can Donor Ligands Make Pd(OAc) ₂ a Stronger Oxidant? Access to Elusive Palladium(II) Reduction Potentials and Effects of Ancillary Ligands via Palladium(II)/Hydroquinone Redox Equilibria Bruns, David L.; Musaev, Djamaladdin G.; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 142, Issue 46 https://doi.org/10.1021/jacs.0c09464	journal	November 2020
Comparison of Quinone‐Based Catholytes for Aqueous Redox Flow Batteries and Demonstration of Long‐Term Stability with Tetrasubstituted Quinones Gerken, James B.; Anson, Colin W.; Preger, Yuliya Advanced Energy Materials, Vol. 10, Issue 20 https://doi.org/10.1002/aenm.202000340	journal	April 2020
Efficient electrochemical synthesis of robust, densely functionalized water soluble quinones Gerken, James B.; Stamoulis, Alexios; Suh, Sung-Eun Chemical Communications, Vol. 56, Issue 8 https://doi.org/10.1039/C9CC08878D	journal	January 2020
Electrochemical Strategy for Hydrazine Synthesis: Development and Overpotential Analysis of Methods for Oxidative N–N Coupling of an Ammonia Surrogate Wang, Fei; Gerken, James B.; Bates, Desiree M. Journal of the American Chemical Society, Vol. 142, Issue 28 https://doi.org/10.1021/jacs.0c04626	journal	June 2020
Electrochemical Oxidation of Organic Molecules at Lower Overpotential: Accessing Broader Functional Group Compatibility with Electron−Proton Transfer Mediators Wang, Fei; Stahl, Shannon S. Accounts of Chemical Research, Vol. 53, Issue 3 https://doi.org/10.1021/acs.accounts.9b00544	journal	February 2020
Deriving the Turnover Frequency of Aminoxyl-Catalyzed Alcohol Oxidation by Chronoamperometry: An Introduction to Organic Electrocatalysis Goes, Shannon L.; Mayer, Mikayla N.; Nutting, Jordan E. Journal of Chemical Education, Vol. 98, Issue 2 https://doi.org/10.1021/acs.jchemed.0c01244	journal	December 2020
“How Should I Think about Voltage? What Is Overpotential?”: Establishing an Organic Chemistry Intuition for Electrochemistry Nutting, Jordan E.; Gerken, James B.; Stamoulis, Alexios G. The Journal of Organic Chemistry, Vol. 86, Issue 22 https://doi.org/10.1021/acs.joc.1c01520	journal	October 2021
Modular Electrochemical Synthesis Using a Redox Reservoir Paired with Independent Half-Reactions Wang, Fengmei; Li, Wenjie; Wang, Rui Joule, Vol. 5, Issue 1 https://doi.org/10.1016/j.joule.2020.11.011	journal	January 2021
Stable Tetrasubstituted Quinone Redox Reservoir for Enhancing Decoupled Hydrogen and Oxygen Evolution Wang, Fei; Sheng, Hongyuan; Li, Wenjie ACS Energy Letters https://doi.org/10.1021/acsenergylett.1c00236	journal	March 2021
Scalable Flow Electrochemical Alcohol Oxidation: Maintaining High Stereochemical Fidelity in the Synthesis of Levetiracetam Zhong, Xing; Hoque, Md Asmaul; Graaf, Matthew D. Organic Process Research & Development, Vol. 25, Issue 12 https://doi.org/10.1021/acs.oprd.1c00036	journal	April 2021
Redox Catalysis Facilitates Lignin Depolymerization Bosque, Irene; Magallanes, Gabriel; Rigoulet, Mathilde ACS Central Science, Vol. 3, Issue 6 https://doi.org/10.1021/acscentsci.7b00140	journal	June 2017
Introduction: Electrochemistry: Technology, Synthesis, Energy, and Materials Little, R. Daniel; Moeller, Kevin D. Chemical Reviews, Vol. 118, Issue 9 https://doi.org/10.1021/acs.chemrev.8b00197	journal	May 2018
Using Physical Organic Chemistry To Shape the Course of Electrochemical Reactions Moeller, Kevin D. Chemical Reviews, Vol. 118, Issue 9 https://doi.org/10.1021/acs.chemrev.7b00656	journal	March 2018
Electrons, Electrodes, and the Transformation of Organic Molecules Francke, Robert; Gonzalez, Luisalberto; Little, R. Daniel https://doi.org/10.1002/9783527822508.ch79	book	January 2020
Organic Electrochemistry: Expanding the Scope of Paired Reactions Wu, Tiandi; Moeller, Kevin D. Angewandte Chemie International Edition, Vol. 60, Issue 23 https://doi.org/10.1002/anie.202100193	journal	May 2021
Electrifying Organic Synthesis Wiebe, Anton; Gieshoff, Tile; Möhle, Sabine Angewandte Chemie International Edition, Vol. 57, Issue 20 https://doi.org/10.1002/anie.201711060	journal	March 2018
Facile and Rapid Room-Temperature Electrosynthesis and Controlled Surface Growth of Fe-MIL-101 and Fe-MIL-101-NH ₂ Wu, Wenbo; Decker, Gerald E.; Weaver, Anna E. ACS Central Science, Vol. 7, Issue 8 https://doi.org/10.1021/acscentsci.1c00686	journal	August 2021
Electrochemically Mediated Syntheses of Titanium(III)-Based Metal–Organic Frameworks Antonio, Alexandra M.; Rosenthal, Joel; Bloch, Eric D. Journal of the American Chemical Society, Vol. 141, Issue 29 https://doi.org/10.1021/jacs.9b05035	journal	June 2019
A journey on the electrochemical road to sustainability Rand, David A. J. Journal of Solid State Electrochemistry, Vol. 15, Issue 7-8 https://doi.org/10.1007/s10008-011-1410-z	journal	June 2011
Synthetic Organic Electrochemistry: An Enabling and Innately Sustainable Method Horn, Evan J.; Rosen, Brandon R.; Baran, Phil S. ACS Central Science, Vol. 2, Issue 5 https://doi.org/10.1021/acscentsci.6b00091	journal	May 2016
Electrosynthesis: Sustainability Is Not Enough Kawamata, Yu; Baran, Phil S. Joule, Vol. 4, Issue 4 https://doi.org/10.1016/j.joule.2020.02.002	journal	April 2020
A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions Ghosh, Munmun; Shinde, Valmik S.; Rueping, Magnus Beilstein Journal of Organic Chemistry, Vol. 15 https://doi.org/10.3762/bjoc.15.264	journal	January 2019
Nitroxyl-mediated electrooxidation of alcohols to aldehydes and ketones Semmelhack, M. F.; Chou, Chuen S.; Cortes, David A. Journal of the American Chemical Society, Vol. 105, Issue 13 https://doi.org/10.1021/ja00351a070	journal	June 1983
Redox mediators as charge agents for changing electrochemical reactions Tamirat, Andebet Gedamu; Guan, Xuze; Liu, Jingyuan Chemical Society Reviews, Vol. 49, Issue 20 https://doi.org/10.1039/D0CS00489H	journal	January 2020
Free Radical Functionalization of Organic Compounds Catalyzed by N- Hydroxyphthalimide ^† Recupero, Francesco; Punta, Carlo Chemical Reviews, Vol. 107, Issue 9 https://doi.org/10.1021/cr040170k	journal	September 2007
Mechanism of Electrochemical Generation and Decomposition of Phthalimide- N -oxyl Yang, Cheng; Farmer, Luke A.; Pratt, Derek A. Journal of the American Chemical Society, Vol. 143, Issue 27 https://doi.org/10.1021/jacs.1c04181	journal	July 2021
Aromatic polyfluoro-compounds—XXXV Coe, P. L.; Croll, B. T.; Patrick, C. R. Tetrahedron, Vol. 23, Issue 1 https://doi.org/10.1016/S0040-4020(01)83336-6	journal	January 1967
Catalytic dehydrative etherification and chlorination of benzyl alcohols in ionic liquids Kalviri, Hassan A.; Petten, Chad F.; Kerton, Francesca M. Chemical Communications, Issue 34 https://doi.org/10.1039/b909866f	journal	January 2009
Halodehydroxylation of alcohols to yield benzylic and alkyl halides in ionic liquids Petten, Chad F.; Kalviri, Hassan A.; Kerton, Francesca M. Sustainable Chemical Processes, Vol. 3, Issue 1 https://doi.org/10.1186/s40508-015-0043-4	journal	October 2015
Dehydration of Benzyl Alcohols in Phosphonium Ionic Liquids: Synthesis of Ethers and Alkenes Kalviri, Hassan A.; Kerton, Francesca M. Advanced Synthesis & Catalysis, Vol. 353, Issue 17 https://doi.org/10.1002/adsc.201100445	journal	November 2011
Electrocatalytic oxidation of alcohols using substituted N-hydroxyphthalimides as catalysts Gorgy, Karine; Lepretre, Jean-Claude; Saint-Aman, Eric Electrochimica Acta, Vol. 44, Issue 2-3 https://doi.org/10.1016/S0013-4686(97)10189-X	journal	September 1998
Kinetics of N -oxyl Radicals’ Decay Kushch, Olga; Hordieieva, Iryna; Novikova, Katerina The Journal of Organic Chemistry, Vol. 85, Issue 11 https://doi.org/10.1021/acs.joc.0c00506	journal	May 2020
Visible-light-mediated photocatalytic cross-coupling of acetenyl ketones with benzyl trifluoroborate Zhang, Lingchun; Chu, Yanle; Ma, Peizhi Organic & Biomolecular Chemistry, Vol. 18, Issue 6 https://doi.org/10.1039/C9OB02624J	journal	January 2020
Electrochemical‐Induced Hydrogenation of Electron‐Deficient Internal Olefins and Alkynes with CH ₃ OH as Hydrogen Donor Qin, Hongyun; Yang, Jianjing; Yan, Kelu Advanced Synthesis & Catalysis, Vol. 363, Issue 8 https://doi.org/10.1002/adsc.202100022	journal	March 2021
Radical chemistry of tert-butyl hydroperoxide (TBHP). Part 1. Studies of the FeIII–TBHP mechanism Barton, Derek H. R.; Le Gloahec, Vale´rie N.; Patin, Henri New Journal of Chemistry, Vol. 22, Issue 6 https://doi.org/10.1039/a709266k	journal	January 1998
Radical chemistry of tert-butyl hydroperoxide (TBHP). Part 2. Studies of the FeII–TBHP mechanism Barton, Derek H. R.; Le Gloahec, Vale´rie N.; Patin, Henri New Journal of Chemistry, Vol. 22, Issue 6 https://doi.org/10.1039/a800562a	journal	January 1998
The radical chemistry of t-butyl hydroperoxide (TBHP) - Part - further studies on hydrocarbon activation Barton, Derek H. R.; Le Gloahec, Vale´rie N. Tetrahedron, Vol. 54, Issue 51 https://doi.org/10.1016/S0040-4020(98)00974-0	journal	December 1998
Naturally Occurring Protein Kinase C Inhibitors; II ¹ . Isolation of Oligomeric Stilbenes from Caragana sinica ² Kulanthaivel, Palaniappan; Janzen, William; Ballas, Lawrence Planta Medica, Vol. 61, Issue 01 https://doi.org/10.1055/s-2006-957996	journal	February 1995
Stilbene Derivatives from Cissus quadrangularis Adesanya, Saburi A.; Nia, René; Martin, Marie-Thérèse Journal of Natural Products, Vol. 62, Issue 12 https://doi.org/10.1021/np9902744	journal	October 1999
Five novel oligostilbenes from the roots of Caragana sinica Luo, Hong-Feng; Zhang, Li-Ping; Hu, Chang-Qi Tetrahedron, Vol. 57, Issue 23 https://doi.org/10.1016/S0040-4020(01)00427-6	journal	June 2001
Concise total syntheses of (±)isopaucifloral F, (±)quadrangularin A, and (±)pallidol Zhong, Chen; Zhu, Jun; Chang, Jun Tetrahedron Letters, Vol. 52, Issue 22 https://doi.org/10.1016/j.tetlet.2011.03.002	journal	June 2011
Antioxidative oligostilbenes from Caragana sinica Jin, Qinghao; Han, Xiang Hua; Hong, Seong Su Bioorganic & Medicinal Chemistry Letters, Vol. 22, Issue 2 https://doi.org/10.1016/j.bmcl.2011.12.012	journal	January 2012
Total Synthesis of Resveratrol-Based Natural Products: A Chemoselective Solution Snyder, Scott A.; Zografos, Alexandros L.; Lin, Yunqing Angewandte Chemie International Edition, Vol. 46, Issue 43 https://doi.org/10.1002/anie.200703333	journal	November 2007
An approach to the synthesis of dimeric resveratrol natural products via a palladium-catalyzed domino reaction Jeffrey, Jenna L.; Sarpong, Richmond Tetrahedron Letters, Vol. 50, Issue 17 https://doi.org/10.1016/j.tetlet.2009.02.067	journal	April 2009
Concise Synthesis of Pauciflorol F Using a Larock Annulation Jeffrey, Jenna L.; Sarpong, Richmond Organic Letters, Vol. 11, Issue 23 https://doi.org/10.1021/ol902141z	journal	November 2009
Aerobic Oxidation of Benzyl Alcohols Catalyzed by Aryl Substituted N- Hydroxyphthalimides. Possible Involvement of a Charge-Transfer Complex Annunziatini, Claudia; Gerini, Maria Francesca; Lanzalunga, Osvaldo The Journal of Organic Chemistry, Vol. 69, Issue 10 https://doi.org/10.1021/jo049887y	journal	April 2004
The Stille Reaction, 38 Years Later Cordovilla, Carlos; Bartolomé, Camino; Martínez-Ilarduya, Jesús M. ACS Catalysis, Vol. 5, Issue 5 https://doi.org/10.1021/acscatal.5b00448	journal	March 2015
Nazarov reaction: current trends and recent advances in the synthesis of natural compounds and their analogs Vinogradov, Maxim G.; Turova, Olga V.; Zlotin, Sergei G. Org. Biomol. Chem., Vol. 15, Issue 39 https://doi.org/10.1039/C7OB01981E	journal	January 2017

Similar Records

Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols

Journal Article · 2022 · Organic Letters · OSTI ID:2510462

Hatch, Chad E.; Martin, Maxwell I.; Gilmartin, Philip H.; +6 more

Base-Assisted Nitrate Mediation as the Mechanism of Electrochemical Benzyl Alcohol Oxidation

Journal Article · 2021 · Journal of Physical Chemistry. C · OSTI ID:1780873

DiMeglio, John L.; Terry, Bradley D.; Breuhaus-Alvarez, Andrew G.; +2 more

Related Subjects

Chemistry

Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols

Citation Formats

References (87)

Similar Records

Related Subjects