التفاصيل البيبلوغرافية
| العنوان: |
Synthesis of 1H‑Isoindole-containing scaffolds enabled by a nitrile trifunctionalization |
| المؤلفون: |
Díaz Jiménez, Àlex, Monreal Corona, Roger, Solà i Puig, Miquel, Poater Teixidor, Albert, Roglans i Ribas, Anna, Pla i Quintana, Anna |
| المساهمون: |
Agencia Estatal de Investigación |
| المصدر: |
ACS Catalysis, 2024, vol. 14, p. 7381-7388 ; Articles publicats (D-Q) ; Díaz Jiménez, Àlex Monreal Corona, Roger Solà i Puig, Miquel Poater Teixidor, Albert Roglans i Ribas, Anna Pla i Quintana, Anna 2024 Synthesis of 1H‑Isoindole-containing scaffolds enabled by a nitrile trifunctionalization ACS Catalysis 14 7381 7388 |
| بيانات النشر: |
American Chemical Society (ACS) |
| سنة النشر: |
2024 |
| المجموعة: |
Universitat de Girona: DUGiDocs (UdG Digital Repository) |
| مصطلحات موضوعية: |
Reaccions químiques, Chemical reactions, Catàlisi homogènia, Rodi, Rhodium, Compostos de nitrogen, Nitrogen compounds, Carbens, Carbenes (Methylene compounds), Funcional de densitat, Teoria del, Density functionals |
| الوصف: |
Nitrogen ring structures are widely found in biologically active compounds and natural products, making their construction an important area of focus in modern organic synthesis. In this work, the synthesis of products containing the 1H-isoindole motif has been successfully accomplished through a rhodium-catalyzed cascade, resulting in a significant increase in molecular complexity. This reaction, which encompasses the trifunctionalization of a nitrile moiety, is triggered by the formation of a nitrile ylide with extended conjugation by reaction of a rhodium vinylcarbene with a nitrile. The mechanism has been investigated by means of density functional theory calculations and supported through experimental data, enabling us to elucidate the precise steps that explain the rare nitrile trifunctionalization. A crucial step in this trifunctionalization is the attack of the second vinylcarbene to the azepine ring formed upon1,7-electrocyclization of the nitrile ylide with extended conjugation ; We are grateful for financial support from the Ministerio de Ciencia e Innovación (PID2021-127423NB-I00 and PID2020-113711GB-I00 MCIN/AEI/10.13039/501100011033 projects) and the Generalitat de Catalunya (Project 2021-SGR-623). We thank the Spanish Ministerio de Universidades for the predoctoral fellowship FPU18/02912 to A.D.-J. and FPU20/00707 to R.M.-C. A.P.Q. and A.P. are Serra Húnter Fellows, and A.P. thanks ICREA Academia Prize 2019 |
| نوع الوثيقة: |
article in journal/newspaper |
| وصف الملف: |
8 p.; application/pdf |
| اللغة: |
English |
| Relation: |
info:eu-repo/semantics/altIdentifier/eissn/2155-5435; PID2021-127423NB-I00; PID2020-113711GB-I00; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2021-127423NB-I00/ES/CATALISIS PREDICTIVA PARA CAMBIAR EL ODEN SECUENCIAL ENTRE EXPERIMENTOS I CALCULOS/; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-113711GB-I00/ES/DISEÑO Y SINTESIS DE FULLERENOS PARA LA CONSTRUCCION DE CELDAS SOLARES HIBRIDAS DE PEROVSKITA Y FULERENOS D ALTO RENDIMIENTO. UN ENFOQUE EXPERIMENTAL Y COMPUTACIONAL SINERGICO/; http://hdl.handle.net/10256/24804 |
| الاتاحة: |
http://hdl.handle.net/10256/24804 |
| Rights: |
Reconeixement 4.0 Internacional ; http://creativecommons.org/licenses/by/4.0 ; info:eu-repo/semantics/openAccess |
| رقم الانضمام: |
edsbas.9552B330 |
| قاعدة البيانات: |
BASE |