دورية أكاديمية
Substrate-Mediator Duality of 1,4-Dicyanobenzene in Electrochemical C(sp 2 )-C(sp 3 ) Bond Formation with Alkyl Bromides.
| العنوان: | Substrate-Mediator Duality of 1,4-Dicyanobenzene in Electrochemical C(sp 2 )-C(sp 3 ) Bond Formation with Alkyl Bromides. |
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| المؤلفون: | Johnston B; Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA., Loh DM; Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA., Nocera DG; Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA. |
| المصدر: | Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2023 Dec 04; Vol. 62 (49), pp. e202312128. Date of Electronic Publication: 2023 Nov 07. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 0370543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3773 (Electronic) Linking ISSN: 14337851 NLM ISO Abbreviation: Angew Chem Int Ed Engl Subsets: PubMed not MEDLINE; MEDLINE |
| أسماء مطبوعة: | Publication: <2004-> : Weinheim : Wiley-VCH Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962- |
| مستخلص: | Electrochemical approaches to form C(sp 2 )-C(sp 3 ) bonds have focused on coupling C(sp 3 ) electrophiles that form stabilized carbon-centered radicals upon reduction or oxidation. Whereas alkyl bromides are desirable C(sp 3 ) coupling partners owing to their availability and cost-effectiveness, their tendency to undergo radical-radical homocoupling makes them challenging substrates for electroreductive cross-coupling. Herein, we disclose a metal-free regioselective cross-coupling of 1,4-dicyanobenzene, a useful precursor to aromatic nitriles, and alkyl bromides. Alkyl bromide reduction is mediated directly by 1,4-dicyanobenzene radical anions, leading to negligible homocoupling and high cross-selectivity to form 1,4-alkyl cyanobenzenes. The cross-coupling scheme is compatible with oxidatively sensitive and acidic functional groups such as amines and alcohols, which have proven difficult to incorporate in alternative electrochemical approaches using carboxylic acids as C(sp 3 ) precursors. (© 2023 Wiley-VCH GmbH.) |
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| معلومات مُعتمدة: | CHE-2243724 National Science Foundation: Directorate for Mathematical and Physical Sciences |
| فهرسة مساهمة: | Keywords: C−C Cross-Coupling; Electrochemistry; Radicals; Redox Mediator |
| تواريخ الأحداث: | Date Created: 20231019 Latest Revision: 20231127 |
| رمز التحديث: | 20231215 |
| DOI: | 10.1002/anie.202312128 |
| PMID: | 37857567 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 1521-3773 |
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| DOI: | 10.1002/anie.202312128 |