Rational design of super reductive EDA photocatalyst for challenging reactions: a theoretical and experimental study

Deng, Yi-Hui; Li, Qini; Li, Manhong; Wang, Leifeng; Sun, Tian-Yu

doi:10.1039/d3ra07558c

Cited by 1 publication

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References 40 publications

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“…Our group has recently described several strategies for generating aryl radicals under visible-light catalysis [39][40][41], and our previous studies have demonstrated that the reductive coupling of isoquinoline and B 2 Pin 2 can produce a dimer. This dimer can coordinate with an organic base (NEt 3 ) in situ to form an EDA complex (Scheme 1d).…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Site-Selective Aryl C-H Borylation with Electron-Donor-Acceptor Complex Derived from B2Pin2 and Isoquinoline

Li,

Deng,

Chang

et al. 2024

Molecules

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Due to boron’s metalloid properties, aromatic boron reagents are prevalent synthetic intermediates. The direct borylation of aryl C-H bonds for producing aromatic boron compounds offers an appealing, one-step solution. Despite significant advances in this field, achieving regioselective aryl C-H bond borylation using simple and readily available starting materials still remains a challenge. In this work, we attempted to enhance the reactivity of the electron-donor-acceptor (EDA) complex by selecting different bases to replace the organic base (NEt3) used in our previous research. To our delight, when using NH4HCO3 as the base, we have achieved a mild visible-light-mediated aromatic C-H bond borylation reaction with exceptional regioselectivity (rr > 40:1 to single isomers). Compared with our previous borylation methodologies, this protocol provides a more efficient and broader scope for aryl C-H bond borylation through the use of N-Bromosuccinimide. The protocol’s good functional-group tolerance and excellent regioselectivity enable the functionalization of a variety of biologically relevant compounds and novel cascade transformations. Mechanistic experiments and theoretical calculations conducted in this study have indicated that, for certain arenes, the aryl C-H bond borylation might proceed through a new reaction mechanism, which involves the formation of a novel transient EDA complex.

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Section: Introductionmentioning

confidence: 99%

Photoinduced Site-Selective Aryl C-H Borylation with Electron-Donor-Acceptor Complex Derived from B2Pin2 and Isoquinoline

Li,

Deng,

Chang

et al. 2024

Molecules

Self Cite

View full text Add to dashboard Cite

show abstract

Rational design of super reductive EDA photocatalyst for challenging reactions: a theoretical and experimental study

Abstract: We have developed a novel electron-donor-acceptor (EDA) photocatalyst through DFT-guided design. This photocatalyst is formed in situ from isoquinoline, a diboron reagent, and a weak base, and can be effectively utilized for challenging reactions.

Cited by 1 publication

References 40 publications

Photoinduced Site-Selective Aryl C-H Borylation with Electron-Donor-Acceptor Complex Derived from B2Pin2 and Isoquinoline

Photoinduced Site-Selective Aryl C-H Borylation with Electron-Donor-Acceptor Complex Derived from B2Pin2 and Isoquinoline

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