Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation

被引：5

作者：

Spils, Julian ^{[1
]}

Wirth, Thomas ^{[2
]}

Nachtsheim, Boris J. ^{[1
]}

机构：

[1] Univ Bremen, Inst Organ & Analyt Chem, Leobener Str 7, D-28359 Bremen, Germany

[2] Cardiff Univ, Sch Chem, Pk Pl,Main Bldg, Cardiff CF10 3AT, Wales

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 19卷

关键词：

electrochemistry; flow chemistry; hypervalent compounds; iodine; oxidation; HYPERVALENT IODINE REAGENTS; ONE-POT SYNTHESIS; DIARYLIODONIUM SALTS; EFFICIENT;

D O I：

10.3762/bjoc.19.2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a multi-step continuous-flow procedure for the generation of six-membered diaryliodonium salts. The accompanying scalability and atom economy are significant improvements to existing batch methods. Benzyl acetates are submitted to this two-step procedure as highly available and cheap starting materials. An acid-catalyzed Friedel-Crafts alkylation followed by an anodic oxidative cyclization yielded a defined set of cyclic iodonium salts in a highly substrate-dependent yield.

引用

页码：27 / 32

页数：6

共 44 条

[1] An Enantioconvergent Benzylic Hydroxylation Using a Chiral Aryl Iodide in a Dual Activation Mode
Abazid, Ayham H.
Clamor, Nils
Nachtsheim, Boris J.
[J]. ACS CATALYSIS, 2020, 10 (15): : 8042 - 8048
[2] A Triazole-Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
Abazid, Ayham H.
Nachtsheim, Boris J.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (04) : 1479 - 1484
[3] Diaryliodonium Salts in Organic Syntheses: A Useful Compound Class for Novel Arylation Strategies
Aradi, Klara
Toth, Balazs L.
Tolnai, Gergely L.
Novak, Zoltan
[J]. SYNLETT, 2016, 27 (10) : 1456 - 1485
[4] Aryl Radical Formation by Copper(I) Photocatalyzed Reduction of Diaryliodonium Salts: NMR Evidence for a CuII/CuI Mechanism
Baralle, Alexandre
Fensterbank, Louis
Goddard, Jean-Philippe
Ollivier, Cyril
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (33) : 10809 - 10813
[5] Regiospecific one-pot synthesis of diaryliodonium tetrafluoroborates from arylboronic acids and aryl iodides
Bielawski, Marcin
Aili, David
Olofsson, Berit
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) : 4602 - 4607
[6] Efficient and general one-pot synthesis of diaryliodonium triflates: Optimization, scope and limitations
Bielawski, Marcin
Zhu, Mingzhao
Olofsson, Berit
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) : 2610 - 2618
[7] Evolution of N-Heterocycle-Substituted Iodoarenes (NHIAs) to Efficient Organocatalysts in Iodine(I/III)-Mediated Oxidative Transformations
Boelke, Andreas
Nachtsheim, Boris J.
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (01) : 184 - 191
[8] One-Pot Synthesis and Conformational Analysis of Six-Membered Cyclic Iodonium Salts
Caspers, Lucien D.
Spils, Julian
Damrath, Mattis
Lork, Enno
Nachtsheim, Boris J.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (14) : 9161 - 9178
[9] Directing-Group-mediated C-H-Alkynylations
Caspers, Lucien D.
Nachtsheim, Boris J.
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (10) : 1231 - 1247
[10] Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents
Charpentier, Julie
Frueh, Natalja
Togni, Antonio
[J]. CHEMICAL REVIEWS, 2015, 115 (02) : 650 - 682

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