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

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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.

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Cited by 2 publications

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“…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 ).…”

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confidence: 99%

Electrochemistry-Enabled C-Heteroatom Bond Formation of Alkyl Germanes

Schoetz,

Deckers,

Singh

et al. 2024

J. Am. Chem. Soc.

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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.

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confidence: 99%

Electrochemistry-Enabled C-Heteroatom Bond Formation of Alkyl Germanes

Schoetz,

Deckers,

Singh

et al. 2024

J. Am. Chem. Soc.

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

Katayama,

Obora

2024

Chemistry Letters

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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.

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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 2 publications

References 100 publications

Electrochemistry-Enabled C-Heteroatom Bond Formation of Alkyl Germanes

Electrochemistry-Enabled C-Heteroatom Bond Formation of Alkyl Germanes

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

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