Reversible C-H bond silylation with a neutral silicon Lewis acid
The silicon-carbon bond is a valuable linchpin for synthetic transformations. However, installing Si-C functionalities requires metalated C-nucleophiles, activated silicon reagents (silylium ions, silyl radicals, and silyl anions), or transition metal catalysis, and it occurs irreversibly. In contra...
Gespeichert in:
| Hauptverfasser: | , |
|---|---|
| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
2023
|
| In: |
Chemical science
Year: 2023, Jahrgang: 14, Heft: 40, Pages: 11237-11242 |
| ISSN: | 2041-6539 |
| DOI: | 10.1039/D3SC03488G |
| Online-Zugang: | Verlag, kostenfrei, Volltext: https://doi.org/10.1039/D3SC03488G Verlag, lizenzpflichtig, Volltext: https://pubs.rsc.org/en/content/articlelanding/2023/sc/d3sc03488g 
|
| Verfasserangaben: | Thaddäus Thorwart and Lutz Greb |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1870636996 | ||
| 003 | DE-627 | ||
| 005 | 20240307041409.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231120s2023 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1039/D3SC03488G |2 doi | |
| 035 | |a (DE-627)1870636996 | ||
| 035 | |a (DE-599)KXP1870636996 | ||
| 035 | |a (OCoLC)1425209454 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 30 |2 sdnb | ||
| 100 | 1 | |a Thorwart, Thaddäus |d 1995- |e VerfasserIn |0 (DE-588)1269529382 |0 (DE-627)1818061880 |4 aut | |
| 245 | 1 | 0 | |a Reversible C-H bond silylation with a neutral silicon Lewis acid |c Thaddäus Thorwart and Lutz Greb |
| 264 | 1 | |c 2023 | |
| 300 | |b Illustrationen | ||
| 300 | |a 6 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Veröffentlicht: 14. September 2023 | ||
| 500 | |a Gesehen am 20.11.2023 | ||
| 520 | |a The silicon-carbon bond is a valuable linchpin for synthetic transformations. However, installing Si-C functionalities requires metalated C-nucleophiles, activated silicon reagents (silylium ions, silyl radicals, and silyl anions), or transition metal catalysis, and it occurs irreversibly. In contrast, spontaneous C-H silylations with neutral silanes leading to anionic silicates, and their reversible deconstruction, are elusive. Herein, the CH-bond silylation of heterocycles or a terminal alkyne is achieved by reaction with bis(perfluoro(N-phenyl-ortho-amidophenolato))silane and 1,2,2,6,6-pentamethylpiperidine. Computational and experimental insights reveal a frustrated Lewis pair (FLP) mechanism. Adding a silaphilic donor to the ammonium silicate products induces the reformation of the C-H bond, thus complementing previously known irreversible C-H bond silylation protocols. Interestingly, the FLP “activated” N-methylpyrrole exhibits “deactivated” features against electrophiles, while a catalytic functionalization is found to be effective only in the absence of a base. | ||
| 700 | 1 | |a Greb, Lutz |e VerfasserIn |0 (DE-588)1043619879 |0 (DE-627)770726526 |0 (DE-576)395158265 |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Chemical science |d Cambridge : RSC, 2010 |g 14(2023), 40, Seite 11237-11242 |h Online-Ressource |w (DE-627)629702934 |w (DE-600)2559110-1 |w (DE-576)325003831 |x 2041-6539 |7 nnas |a Reversible C-H bond silylation with a neutral silicon Lewis acid |
| 773 | 1 | 8 | |g volume:14 |g year:2023 |g number:40 |g pages:11237-11242 |g extent:6 |a Reversible C-H bond silylation with a neutral silicon Lewis acid |
| 856 | 4 | 0 | |u https://doi.org/10.1039/D3SC03488G |x Verlag |x Resolving-System |z kostenfrei |3 Volltext |
| 856 | 4 | 0 | |u https://pubs.rsc.org/en/content/articlelanding/2023/sc/d3sc03488g |x Verlag |z lizenzpflichtig |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20231120 | ||
| 993 | |a Article | ||
| 994 | |a 2023 | ||
| 998 | |g 1043619879 |a Greb, Lutz |m 1043619879:Greb, Lutz |d 120000 |d 120200 |d 120000 |e 120000PG1043619879 |e 120200PG1043619879 |e 120000PG1043619879 |k 0/120000/ |k 1/120000/120200/ |k 0/120000/ |p 2 |y j | ||
| 998 | |g 1269529382 |a Thorwart, Thaddäus |m 1269529382:Thorwart, Thaddäus |d 120000 |d 120200 |e 120000PT1269529382 |e 120200PT1269529382 |k 0/120000/ |k 1/120000/120200/ |p 1 |x j | ||
| 999 | |a KXP-PPN1870636996 |e 4413905490 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"type":{"bibl":"article-journal","media":"Online-Ressource"},"title":[{"title_sort":"Reversible C-H bond silylation with a neutral silicon Lewis acid","title":"Reversible C-H bond silylation with a neutral silicon Lewis acid"}],"name":{"displayForm":["Thaddäus Thorwart and Lutz Greb"]},"origin":[{"dateIssuedKey":"2023","dateIssuedDisp":"2023"}],"person":[{"family":"Thorwart","display":"Thorwart, Thaddäus","role":"aut","given":"Thaddäus"},{"given":"Lutz","role":"aut","display":"Greb, Lutz","family":"Greb"}],"id":{"eki":["1870636996"],"doi":["10.1039/D3SC03488G"]},"note":["Veröffentlicht: 14. September 2023","Gesehen am 20.11.2023"],"language":["eng"],"physDesc":[{"extent":"6 S.","noteIll":"Illustrationen"}],"recId":"1870636996","relHost":[{"physDesc":[{"extent":"Online-Ressource"}],"recId":"629702934","note":["Gesehen am 04.11.25"],"corporate":[{"display":"Royal Society of Chemistry","role":"isb"}],"type":{"media":"Online-Ressource","bibl":"periodical"},"pubHistory":["1.2010 -"],"language":["eng"],"origin":[{"dateIssuedDisp":"2010-","publisherPlace":"Cambridge","dateIssuedKey":"2010","publisher":"RSC"}],"id":{"eki":["629702934"],"issn":["2041-6539"],"zdb":["2559110-1"]},"part":{"pages":"11237-11242","text":"14(2023), 40, Seite 11237-11242","year":"2023","volume":"14","extent":"6","issue":"40"},"disp":"Reversible C-H bond silylation with a neutral silicon Lewis acidChemical science","title":[{"title":"Chemical science","title_sort":"Chemical science"}],"name":{"displayForm":["RSC, Royal Society of Chemistry"]}}]} | ||
| SRT | |a THORWARTTHREVERSIBLE2023 | ||