Visible-Light-Induced Siloxycarbene Addition to N═N of Azodicarboxylates : Synthesis of Acyl Hydrazides from Acylsilanes
We report the synthesis of acyl hydrazides from acylsilanes in the presence of visible light without the aid of additives or transition metals. Acylsilanes underwent [1,2]-Brook rearrangement to generate the nucleophilic siloxycarbenes which on further addition to N═N of azodicarboxylates produced the acyl hydrazides. Control experiments indicate that the reaction proceeds through the singlet carbene intermediate. Transformation of the acyl hydrazide functionality to other functional groups was demonstrated, including the synthesis of the drug candidate Moclobemide.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2024 |
|---|---|
| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
|---|---|
| Enthalten in: |
Organic letters - 26(2024), 10 vom: 15. März, Seite 2039-2044 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Saleem, Mohammad [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
|---|
| Anmerkungen: |
Date Revised 15.03.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
|---|
| doi: |
10.1021/acs.orglett.4c00185 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM369761812 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM369761812 | ||
| 003 | DE-627 | ||
| 005 | 20240315234630.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 240315s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1021/acs.orglett.4c00185 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1330.xml |
| 035 | |a (DE-627)NLM369761812 | ||
| 035 | |a (NLM)38486498 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Saleem, Mohammad |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Visible-Light-Induced Siloxycarbene Addition to N═N of Azodicarboxylates |b Synthesis of Acyl Hydrazides from Acylsilanes |
| 264 | 1 | |c 2024 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Revised 15.03.2024 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a We report the synthesis of acyl hydrazides from acylsilanes in the presence of visible light without the aid of additives or transition metals. Acylsilanes underwent [1,2]-Brook rearrangement to generate the nucleophilic siloxycarbenes which on further addition to N═N of azodicarboxylates produced the acyl hydrazides. Control experiments indicate that the reaction proceeds through the singlet carbene intermediate. Transformation of the acyl hydrazide functionality to other functional groups was demonstrated, including the synthesis of the drug candidate Moclobemide | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Ratwan, Akash |e verfasserin |4 aut | |
| 700 | 1 | |a Yamini, Pokhriyal |e verfasserin |4 aut | |
| 700 | 1 | |a Yadagiri, Dongari |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Organic letters |d 1999 |g 26(2024), 10 vom: 15. März, Seite 2039-2044 |w (DE-627)NLM106817639 |x 1523-7052 |7 nnns |
| 773 | 1 | 8 | |g volume:26 |g year:2024 |g number:10 |g day:15 |g month:03 |g pages:2039-2044 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1021/acs.orglett.4c00185 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 26 |j 2024 |e 10 |b 15 |c 03 |h 2039-2044 | ||