Literature DB >> 35148118

Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols.

Chad E Hatch1, Maxwell I Martin1, Philip H Gilmartin1, Lu Xiong1, Danielle J Beam1, Glenn P A Yap1, Matthew J Von Bargen1, Joel Rosenthal1, William J Chain1.   

Abstract

The electrochemical oxidation of sensitive propargylic benzylic alcohols having varying substituents is reported. We describe the preparation and characterization of N-hydroxytetrafluorophthalimide (TFNHPI) and pseudo-high-throughput development of a green electrochemical oxidation protocol for sensitive propargylic benzylic alcohols that employs TFNHPI as a stable electrochemical mediator. The electrochemical oxidation of propargylic benzylic alcohols was leveraged to develop short synthetic pathways for preparing gram quantities of resveratrol natural products such as pauciflorols.

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Year:  2022        PMID： 35148118      PMCID： PMC9097598          DOI： 10.1021/acs.orglett.1c03860

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.072


  63 in total

1.  Free radical functionalization of organic compounds catalyzed by N-hydroxyphthalimide.

Authors:  Francesco Recupero; Carlo Punta
Journal:  Chem Rev       Date:  2007-09       Impact factor: 60.622

2.  Organic Electrochemistry: Expanding the Scope of Paired Reactions.

Authors:  Tiandi Wu; Kevin D Moeller
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-01       Impact factor: 15.336

3.  Electrochemically Enabled, Nickel-Catalyzed Amination.

Authors:  Chao Li; Yu Kawamata; Hugh Nakamura; Julien C Vantourout; Zhiqing Liu; Qinglong Hou; Denghui Bao; Jeremy T Starr; Jinshan Chen; Ming Yan; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-14       Impact factor: 15.336

4.  Total synthesis of Myc-IV(C16:0, S) via automated electrochemical assembly.

Authors:  Kumpei Yano; Toshiyuki Itoh; Toshiki Nokami
Journal:  Carbohydr Res       Date:  2020-04-18       Impact factor: 2.104

5.  Asymmetric Total Syntheses of 8,9-Seco-ent-kaurane Diterpenoids Enabled by an Electrochemical ODI-[5+2] Cascade.

Authors:  Bingnan Wang; Zhaobo Liu; Zhenzhong Tong; Beiling Gao; Hanfeng Ding
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-04       Impact factor: 15.336

6.  Scalable Flow Electrochemical Alcohol Oxidation: Maintaining High Stereochemical Fidelity in the Synthesis of Levetiracetam.

Authors:  Xing Zhong; Md Asmaul Hoque; Matthew D Graaf; Kaid C Harper; Fei Wang; J David Genders; Shannon S Stahl
Journal:  Org Process Res Dev       Date:  2021-04-19       Impact factor: 3.317

Review 7.  Nazarov reaction: current trends and recent advances in the synthesis of natural compounds and their analogs.

Authors:  Maxim G Vinogradov; Olga V Turova; Sergei G Zlotin
Journal:  Org Biomol Chem       Date:  2017-10-11       Impact factor: 3.876

8.  Electroreductive Olefin-Ketone Coupling.

Authors:  Pengfei Hu; Byron K Peters; Christian A Malapit; Julien C Vantourout; Pan Wang; Jinjun Li; Lucas Mele; Pierre-Georges Echeverria; Shelley D Minteer; Phil S Baran
Journal:  J Am Chem Soc       Date:  2020-12-01       Impact factor: 15.419

9.  "How Should I Think about Voltage? What Is Overpotential?": Establishing an Organic Chemistry Intuition for Electrochemistry.

Authors:  Jordan E Nutting; James B Gerken; Alexios G Stamoulis; David L Bruns; Shannon S Stahl
Journal:  J Org Chem       Date:  2021-10-05       Impact factor: 4.354

10.  Redox Catalysis Facilitates Lignin Depolymerization.

Authors:  Irene Bosque; Gabriel Magallanes; Mathilde Rigoulet; Markus D Kärkäs; Corey R J Stephenson
Journal:  ACS Cent Sci       Date:  2017-06-07       Impact factor: 14.553
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