Copper Photoredox Catalyzed A3’ Coupling of Arylamines, Terminal Alkynes, and Alcohols through a Hydrogen Atom Transfer Process

Sagadevan, Arunachalam; Pampana, V. Kishore Kumar; Hwang, Kuo Chu

doi:10.1002/anie.201813315

Cited by 70 publications

(36 citation statements)

References 50 publications

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“…Very recently, a CuCl-catalyzed three-component reaction between N-alkylanilines, terminal alkynes, and primary alcohols in the presence of stoichiometric benzoquinone as an oxidant to furnish propargylamines is reported by the same group (Fig. 4B, iii) (45). The photoexcited Cu(I)-phenylacetylide reduces benzoquinone, and then the corresponding radical anion species triggers a hydrogen atom transfer process with a primary alcohol to generate an a-oxy radical.…”

Section: C(sp 3 /Sp 2 )-Heteroatom Cross-couplingmentioning

confidence: 89%

Copper’s rapid ascent in visible-light photoredox catalysis

Hossain

Bhattacharyya

Reiser

2019

Science

543

302

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Visible-light photoredox catalysis offers a distinct activation mode complementary to thermal transition metal catalyzed reactions. The vast majority of photoredox processes capitalizes on precious metal ruthenium(II) or iridium(III) complexes that serve as single-electron reductants or oxidants in their photoexcited states. As a low-cost alternative, organic dyes are also frequently used but in general suffer from lower photostability. Copper-based photocatalysts are rapidly emerging, offering not only economic and ecological advantages but also otherwise inaccessible inner-sphere mechanisms, which have been successfully applied to challenging transformations. Moreover, the combination of conventional photocatalysts with copper(I) or copper(II) salts has emerged as an efficient dual catalytic system for cross-coupling reactions.

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Section: C(sp 3 /Sp 2 )-Heteroatom Cross-couplingmentioning

confidence: 89%

Copper’s rapid ascent in visible-light photoredox catalysis

Hossain

Bhattacharyya

Reiser

2019

Science

543

302

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“…28 The group has also achieved the first successful coupling of N-alkylanilines, terminal alkynes, and alcohols via a visible light-mediated copper-catalyzed photoredox-hydrogen atom transfer (HAT) process for facile synthesis of propargyl-amines (Scheme 14). 29 The proposed reaction mechanism is shown in figure 6. The long-lived excited Cu(I)-phenylacetylide serves as an electron donor and transfers an electron to BQ to generate a persistent BQ radical anion and 70.…”

Section: Oxidative Coupling Reactionsmentioning

confidence: 99%

Recent Advances in Visible-Light-Promoted Copper Catalysis in Organic Reactions

Xiong

Xiao

et al. 2021

Synthesis

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In recent years, visible-light-mediated copper photocatalysis have emerged as an attractive strategy for the diverse constructions of basic bonds in an ecologically benign and cost-effective fashion. The intense activity and increasing work of these areas stimulated the exploit of the distinctive properties of copper photocatalysis and the rapid development and expansion of their applications. In this review, we focus on introducing a series of significant achievements in copper complexes as standalone photocatalysis in organic reactions to make an attempt to exhibit their potential capabilities and high flexibilities in synthetic chemistry.

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“…Perhaps the most striking feature of this transformation is the formation of the transient -oxy radical by -C-H bond derivatization of the unactivated alcohol via a HAT process, instead of its direct oxidation to the corresponding aldehyde. 70…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Recent Advances on Copper-Catalyzed C–C Bond Formation via C–H Functionalization

Almasalma

Mejía

2020

Synthesis

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Reactions that form C–C bonds are at the heart of many important transformations, both in industry and in academia. From the myriad of catalytic approaches to achieve such transformations, those relying on C–H functionalization are gaining increasing interest due to their inherent sustainable nature. In this short review, we showcase the most recent advances in the field of C–C bond formation via C–H functionalization, but focusing only on those methodologies relying on copper catalysts. This coinage metal has gained increased popularity in recent years, not only because it is cheaper and more abundant than precious metals, but also thanks to its rich and versatile chemistry.1 Introduction2 Cross-Dehydrogenative Coupling under Thermal Conditions2.1 C(sp3)–C(sp3) Bond Formation2.2 C(sp3)–C(sp2) Bond Formation2.3 C(sp2)–C(sp2) Bond Formation2.4 C(sp3)–C(sp) Bond Formation3 Cross-Dehydrogenative Coupling under Photochemical Conditions3.1 C(sp3)–C(sp3) Bond Formation3.2 C(sp3)–C(sp2) and C(sp3)–C(sp) Bond Formation4 Conclusion and Perspective

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Copper Photoredox Catalyzed A3’ Coupling of Arylamines, Terminal Alkynes, and Alcohols through a Hydrogen Atom Transfer Process

Cited by 70 publications

References 50 publications

Copper’s rapid ascent in visible-light photoredox catalysis

Copper’s rapid ascent in visible-light photoredox catalysis

Recent Advances in Visible-Light-Promoted Copper Catalysis in Organic Reactions

Recent Advances on Copper-Catalyzed C–C Bond Formation via C–H Functionalization

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