Academic Journal
Electrocatalytic Asymmetric Nozaki–Hiyama–Kishi Decarboxylative Coupling: Scope, Applications, and Mechanism
| العنوان: | Electrocatalytic Asymmetric Nozaki–Hiyama–Kishi Decarboxylative Coupling: Scope, Applications, and Mechanism |
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| المؤلفون: | Yang Gao, Baiyang Jiang, Nathan C. Friede, Arianne C. Hunter, Dylan G. Boucher, Shelley D. Minteer, Matthew S. Sigman, Sarah E. Reisman, Phil S. Baran |
| سنة النشر: | 2024 |
| مصطلحات موضوعية: | Biochemistry, Medicine, Microbiology, Genetics, Molecular Biology, Biotechnology, Plant Biology, Environmental Sciences not elsewhere classified, Biological Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, using catalytic tetrakis, mild reductive electrolysis, mechanistic studies revealed, key reductive mediator, electrocatalytic decarboxylative approach, chiral secondary alcohols, asymmetric alkyl e, alkyl nucleophile synthons, via redox, successfully applied, organic reductants, natural products, high enantioselectivity, good yield, functional groups, enabling additives, dramatically simplify, disclosed herein, coupling reactions, broad range |
| الوصف: | The first general enantioselective alkyl-Nozaki–Hiyama–Kishi (NHK) coupling reactions are disclosed herein by employing a Cr-electrocatalytic decarboxylative approach. Using easily accessible aliphatic carboxylic acids (via redox-active esters) as alkyl nucleophile synthons, in combination with aldehydes and enabling additives, chiral secondary alcohols are produced in a good yield with high enantioselectivity under mild reductive electrolysis. This reaction, which cannot be mimicked using stoichiometric metal or organic reductants, tolerates a broad range of functional groups and is successfully applied to dramatically simplify the synthesis of multiple medicinally relevant structures and natural products. Mechanistic studies revealed that this asymmetric alkyl e-NHK reaction was enabled by using catalytic tetrakis(dimethylamino)ethylene, which acts as a key reductive mediator to mediate the electroreduction of the Cr III /chiral ligand complex. |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | unknown |
| Relation: | https://figshare.com/articles/journal_contribution/Electrocatalytic_Asymmetric_Nozaki_Hiyama_Kishi_Decarboxylative_Coupling_Scope_Applications_and_Mechanism/25176544 |
| DOI: | 10.1021/jacs.3c13442.s001 |
| الاتاحة: | https://doi.org/10.1021/jacs.3c13442.s001 https://figshare.com/articles/journal_contribution/Electrocatalytic_Asymmetric_Nozaki_Hiyama_Kishi_Decarboxylative_Coupling_Scope_Applications_and_Mechanism/25176544 |
| Rights: | CC BY-NC 4.0 |
| رقم الانضمام: | edsbas.E3201DDF |
| قاعدة البيانات: | BASE |
| DOI: | 10.1021/jacs.3c13442.s001 |
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