2022
DOI: 10.1038/s41467-022-33602-4
|View full text |Cite
|
Sign up to set email alerts
|

Photoredox-catalyzed C–C bond cleavage of cyclopropanes for the formation of C(sp3)–heteroatom bonds

Abstract: Sterically congested C–O and C–N bonds are ubiquitous in natural products, pharmaceuticals, and bioactive compounds. However, the development of a general method for the efficient construction of those sterically demanding covalent bonds still remains a formidable challenge. Herein, a photoredox-driven ring-opening C(sp3)–heteroatom bond formation of arylcyclopropanes is presented, which enables the construction of structurally diversified while sterically congested dialkyl ether, alkyl ester, alcohol, amine, … Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1

Citation Types

0
18
0

Year Published

2022
2022
2024
2024

Publication Types

Select...
10

Relationship

4
6

Authors

Journals

citations
Cited by 33 publications
(20 citation statements)
references
References 69 publications
(50 reference statements)
0
18
0
Order By: Relevance
“…This method permits the expedient construction of a host of structurally diverse, sterically congested, dialkyl ether, alkyl ester, alcohol, amine, chloro, fluoro, azide, or thiocyanate derivatives (Scheme 4a ). 11 The synthetic utility of this method was further showcased by a late-stage functionalization of several natural products and derivatives of pharmaceutical molecules. In accordance with our previous report, reactions of two enantioenriched cyclopropanes also afforded the desired products with full conservation of their enantiopurity (Scheme 4b ).…”
Section: Photoredox-catalyzed Hydroheterofunctionalization Of Aryl Cy...mentioning
confidence: 99%
“…This method permits the expedient construction of a host of structurally diverse, sterically congested, dialkyl ether, alkyl ester, alcohol, amine, chloro, fluoro, azide, or thiocyanate derivatives (Scheme 4a ). 11 The synthetic utility of this method was further showcased by a late-stage functionalization of several natural products and derivatives of pharmaceutical molecules. In accordance with our previous report, reactions of two enantioenriched cyclopropanes also afforded the desired products with full conservation of their enantiopurity (Scheme 4b ).…”
Section: Photoredox-catalyzed Hydroheterofunctionalization Of Aryl Cy...mentioning
confidence: 99%
“…In 2022, Feng and co-workers 33 demonstrated the photoredox catalyzed C(sp 3 )–heteroatom bond formation reaction via ring opening functionalization of electronically unbiased aryl cyclopropanes 23a . After irradiating several photocatalysts in the presence of a blue LED, the acridinium photocatalyst ( E 1/2 (Acr*/Acr − ) = +2.08 V vs. SCE) proved to be the best to offer product 23c in up to 95% yield (Scheme 23).…”
Section: Carbon-centered Radical Reactionsmentioning
confidence: 99%
“…During the past few decades, many gem -difluorocyclopropanation approaches via the difluorocarbene process have been developed, enabling their further transformations . In this regard, Feng and co-workers have developed a series of photoredox-catalyzed carbon–carbon (C–C) bond cleavage-functionalization of cyclopropanes . Although the transition-metal-catalyzed ring opening of gem -difluorocyclopropane generally afforded defluorinated products (Scheme c), the photoredox-induced C–C bond cleavage of gem -difluorocyclopropane in the presence of Et 3 N·3HF furnished trifluoromethylated products (Scheme d).…”
Section: Introductionmentioning
confidence: 99%