Allylsilane as a versatile handle in photoredox catalysis

Lal, Nand; Shirsath, Sanket B.; Singh, Puja; Deepshikha,; Shaikh, Aslam C.

doi:10.1039/d4cc00734d

Chem. Commun.

2024

DOI: 10.1039/d4cc00734d

|View full text |Cite

Allylsilane as a versatile handle in photoredox catalysis

Nand Lal,

Sanket B. Shirsath,

Puja Singh

et al.

Abstract: This review briefly summarizes the utilization of allylsilane in photoredox catalysis. It highlights the underlying mechanisms for the formation of the C–C/C–heteroatom bond with various functionalities in mild conditions with high selectivity.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article3

Relationship

Self Cite0

Independent3

Authors

Journals

Cited by 3 publications

(1 citation statement)

References 100 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Fluorination using KHF 2 and 18-crown-6 was also feasible ( 46 ). With carbon-based nucleophiles, such as silyl enol ether or allyl silane, C(sp 3 )–C(sp 3 ) bond formations could also be done ( 47 , 48 ).…”

mentioning

confidence: 99%

Electrochemistry-Enabled C-Heteroatom Bond Formation of Alkyl Germanes

Schoetz,

Deckers,

Singh

et al. 2024

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Because of their robustness and orthogonal reactivity features, alkyl germanes bear significant potential as functional handles for the construction of C(sp 3 )-rich scaffolds, especially in the context of modular synthetic approaches. However, to date, only radical-based reactivity has been accessible from these functional handles, which limits the types of possible decorations. Here, we describe the first general C(sp 3 )−heteroatom bond formation of alkyl germanes (−GeEt 3 ) by leveraging electrochemistry to unlock polar reactivity. This approach allowed us to couple C(sp 3 )−GeEt 3 with a variety of nucleophiles to construct ethers, esters, amines, amides, sulfonamides, sulfides, as well as C−P, C−F, and C−C bonds. The compatibility of the electrochemical approach with a modular synthetic strategy of a C 1 motif was also showcased, involving the sequential functionalization of Cl, Bpin, and ultimately GeEt 3 via electrochemistry.

show abstract

mentioning

confidence: 99%

Electrochemistry-Enabled C-Heteroatom Bond Formation of Alkyl Germanes

Schoetz,

Deckers,

Singh

et al. 2024

J. Am. Chem. Soc.

View full text Add to dashboard Cite

show abstract

Organophotocatalyzed C−Si Bond Fragmentation Using Silyl Ethers as Radical Precursors

Luguera Ruiz,

Benazzi,

Tucci

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

In this work, silyl ethers of phenols and alcohols have been successfully prepared and tested as neutral carbon (silicon) centered radical precursors. The organocophotocatalyzed oxidation (by the Fukuzumi catalyst) of these ethers caused the cleavage of a C‐Si (or a Si‐Si) bond for the release of the desired radical to be used for the forging of C(sp3)‐C(sp3) (or C(sp3)‐Si) bonds via a Giese reaction.

show abstract

Developments in the synthesis of allylsilanes by transition metal–catalyzed silylation of 1,3-dienes with disilanes

Katayama,

Obora

2024

Chemistry Letters

View full text Add to dashboard Cite

This highlight review overviews developments in the synthesis of allylsilanes by transition metal–catalyzed silylation of 1,3-dienes with disilanes. We specifically review disilylation, which installs 2 silicon atoms, and silyl-functionalization, which installs both silicon and another atom using disilanes and reagents such as nucleophiles and electrophiles. Utilizing these methods for the silylation of 1,3-dienes provides a robust protocol for the efficient synthesis of the desired allylsilanes in 1 step, thereby streamlining the silyl-functionalization of 1,3-dienes.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Allylsilane as a versatile handle in photoredox catalysis

Abstract: This review briefly summarizes the utilization of allylsilane in photoredox catalysis. It highlights the underlying mechanisms for the formation of the C–C/C–heteroatom bond with various functionalities in mild conditions with high selectivity.

Cited by 3 publications

References 100 publications

Electrochemistry-Enabled C-Heteroatom Bond Formation of Alkyl Germanes

Electrochemistry-Enabled C-Heteroatom Bond Formation of Alkyl Germanes

Organophotocatalyzed C−Si Bond Fragmentation Using Silyl Ethers as Radical Precursors

Developments in the synthesis of allylsilanes by transition metal–catalyzed silylation of 1,3-dienes with disilanes

Contact Info

Product

Resources

About