Visible-light-driven PhSSPh-catalysed regioselective hydroborylation of α,β-unsaturated carbonyl compounds with NHC-boranes

Liu, Xinghua; Shen, Yue; Lu, Cheng Hsien; Jian, Yongchan; Xia, Shuangshuang; Gao, Zhifeng; Zheng, Yuqian; An, Yuanyuan; Wang, Yubin

doi:10.1039/d2cc02846h

Cited by 21 publications

(15 citation statements)

References 56 publications

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“…44 During the preparation of our manuscript, the Wang group reported an elegant regioselective hydroboration of α,β-unsaturated carbonyl compounds using PhSSPh as the catalyst. 45 Although prominent, NHC-borane reacting with other electron-deficient alkenes has remained less explored. In particular, our work can be suitable for a broad electron-deficient alkene, which is timely and attractive.…”

Section: Introductionmentioning

confidence: 99%

Visible-light-induced 1,2-diphenyldisulfane-catalyzed regioselective hydroboration of electron-deficient alkenes

et al. 2022

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Section: Introductionmentioning

confidence: 99%

Visible-light-induced 1,2-diphenyldisulfane-catalyzed regioselective hydroboration of electron-deficient alkenes

et al. 2022

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“…Based on our experimental findings and previous literature precedents, , the most feasible mechanism was proposed in Scheme . First, thiol can react with NHC–BH 3 to produce a key intermediate I , then visible-light-irradiation-induced homolytic cleavage of intermediate I affords a thiyl radical II and an NHC-boryl radical III .…”

Section: Resultsmentioning

confidence: 99%

“…By using NHC–BH 3 as a source of boryl radical, Curran and co-workers disclosed photoinduced 1,4-hydroborylation reactions of electron-efficient aromatics such as dicyanobenzene, cyanopyridines, and dicyanothiophenes with NHC–BH 3 (Scheme c) . Very recently, our group reported a visible-light-driven diphenyl disulfide-catalyzed regioselective hydroborylation reactions of α,β-unsaturated carbonyl compounds with NHC–BH 3 ; this transformation showed a broad range of substrates and afforded a series of α-borylcarbonyl molecules in good to excellent yields (Scheme d) …”

Section: Introductionmentioning

confidence: 99%

Visible-Light-Promoted Regioselective Hydroborylation of Ketene Dithioacetals with NHC-Boranes

An,

Li,

Xia

et al. 2023

J. Org. Chem.

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NHC-boranes have been treated as a reliable source of boryl radicals. In this study, regioselective hydroborylation of ketene dithioacetals with NHC-borane was achieved under mild conditions via a visible-lightpromoted radical chain process using thiophenol as a proton donor and hydrogen atom transfer. This protocol features a low-cost catalyst, good functional group tolerance, a relatively broad range of substrate scope, and good to excellent yields. Moreover, mechanism of this hydroborylation reaction was preliminarily studied.

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“…In 2022, Wang et al reported that visible light induced the regioselective hydroborylation of α , β -unsaturated carbonyl compounds with NHC-boranes, using (PhS) 2 as the photocatalyst. This system could be conducted by blue LED light irradiation, and a variety of α -borylcarbonyl compounds could be obtained in good to excellent yields (Equation (4)) [ 115 ]. …”

Section: Boron-centered Interelement Compounds In Radical Addition Re...mentioning

confidence: 99%

Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process

Yamamoto

2023

Molecules

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In recent years, the importance of “environmentally friendly manufacturing” has been increasing toward the establishment of a resource-recycling society. In organic synthesis, as well, it is becoming increasingly important to develop new synthetic strategies with resource conservation and the recycling of elemental resources in mind, rather than just only synthesis. Many studies on the construction of frameworks of functional molecules using ionic reactions and transition-metal-catalyzed reactions have been reported, but most of them have focused on the formation of carbon–carbon bonds. However, it is essential to introduce appropriate functional groups at appropriate positions in molecules in order for the molecules to express their functions, and furthermore, the highly selective preparation of multiple functional groups is considered important for the creation of new functional molecules. In this review, we focus on radical reactions with high functional group selectivity and overview the recent progress in practical methods for the simultaneous introduction of multiple functional groups and propose future synthetic strategies that emphasize the recycling of elemental resources and environmental friendliness.

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Visible-light-driven PhSSPh-catalysed regioselective hydroborylation of α,β-unsaturated carbonyl compounds with NHC-boranes

Abstract: A photo-induced transition-metal-free regioselective hydroborylation of α,β-unsaturated carbonyl compounds is developed. The PhSSPh reagent was employed as the photocatalyst, and NHC-BH3 was used as the boron source. This transformation shows...

Cited by 21 publications

References 56 publications

Visible-light-induced 1,2-diphenyldisulfane-catalyzed regioselective hydroboration of electron-deficient alkenes

Visible-light-induced 1,2-diphenyldisulfane-catalyzed regioselective hydroboration of electron-deficient alkenes

Visible-Light-Promoted Regioselective Hydroborylation of Ketene Dithioacetals with NHC-Boranes

Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process

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