Dehydrogenative coupling reactions catalysed by Rose Bengal using visible light irradiation

Pan, Yuanhang; Kee, Choon Wee; Chen, Li; Tan, Choon‐Hong

doi:10.1039/c1gc15489c

Cited by 245 publications

(129 citation statements)

References 42 publications

Supporting

Mentioning

121

Contrasting

Unclassified

Order By: Relevance

“…When either electron donating or withdrawing group was introduced into the aromatic ring, slightly improved diastereoselectivities were observed. In contrast to previous reports, 9,[34][35][36][37][38][39] when nitromethane was used as solvent under the standard conditions in the absence of dipolarophiles 89, only the oxidation of 88 to generate the corresponding amides was observed together with recovered starting materials 88 after 2 days.…”

Section: [3 + 2] Reactionscontrasting

confidence: 83%

“…Both RB and GO in photoredox catalysis were proved to be indispensable for high catalytic performance (accelerated rates and increased yields). In disaccord with their previous studies, 39 4-methyl N,N-dimethylaniline was subjected to the reaction conditions to afford the desired products in good yields. The improvement and efficiency of the combination of RB and GO (e.g., 18 and 19) were observed even on the more challenging substrates such as trialkyl amines.…”

Section: ð3þmentioning

confidence: 95%

See 1 more Smart Citation

Photoredox functionalization of C–H bonds adjacent to a nitrogen atom

2012

View full text Add to dashboard Cite

The functionalization of C-H bonds and the visible light photoredox catalysis represent two prominent challenges in organic chemistry. In this regard, the combination of visible-light catalysis and C-H bond functionalization adjacent to a tertiary amine has been successfully developed in the past three years. In this tutorial review, we aim to give a brief overview of this issue and state the main results obtained in the reactions.

show abstract

Section: [3 + 2] Reactionscontrasting

confidence: 83%

Section: ð3þmentioning

confidence: 95%

Photoredox functionalization of C–H bonds adjacent to a nitrogen atom

2012

View full text Add to dashboard Cite

show abstract

“…XXXX, XXX, XXX−XXX were used as the reaction solvent. The method reported by Tan (method 3b) featured the cooperative use of rose bengal and pyrrolidine as an organocatalyst to catalytically generate an enamine nucleophile (Scheme 122 and Scheme 123) 436. This advance enabled ketones to be employed as coupling partners and portends the possibility of an enantioselective coupling,10.1021/acs.chemrev.6b00057 Chem.…”

mentioning

confidence: 98%

Organic Photoredox Catalysis

2016

View full text Add to dashboard Cite

In this review, we highlight the use of organic photoredox catalysts in a myriad of synthetic transformations with a range of applications. This overview is arranged by catalyst class where the photophysics and electrochemical characteristics of each is discussed to underscore the differences and advantages to each type of single electron redox agent. We highlight both net reductive and oxidative as well as redox neutral transformations that can be accomplished using purely organic photoredox-active catalysts. An overview of the basic photophysics and electron transfer theory is presented in order to provide a comprehensive guide for employing this class of catalysts in photoredox manifolds.

show abstract

“…Rose Bengal (RB) was widely used as a visible light-activated photocatalyst [32][33][34][35][36][37][38][39][40][41][42][43][44]. Tan's group studied the photoredox catalysis using RB [32][33][34][35][36].…”

Section: Rose Bengalmentioning

confidence: 99%

“…Tan's group studied the photoredox catalysis using RB [32][33][34][35][36]. RB was a good catalyst for the dehydrogenative coupling reaction between tetrahydroisoquinolines and nitroalkanes ( Figure 9) [33].…”

Section: Rose Bengalmentioning

confidence: 99%

Organic Reactions Promoted by Metal-Free Organic Dyes Under Visible Light Irradiation

Miyabe¹

2018

Visible-Light Photocatalysis of Carbon-Based Materials

View full text Add to dashboard Cite

Although dyes have received much attention as the visible light-activated photocatalysts, the use of metal-free organic dyes in synthetic organic chemistry is still limited. This chapter summarizes the recent progress in the visible light photocatalysis promoted by metalfree organic dyes. Eosin Y is the typical organic dyes to induce the photoredox catalysis. Recently, other organic dyes such as Rose Bengal, fluorescein, and methylene blue have been studied as photocatalysts to promote the single-electron transfer processes.

show abstract

Dehydrogenative coupling reactions catalysed by Rose Bengal using visible light irradiation

Cited by 245 publications

References 42 publications

Photoredox functionalization of C–H bonds adjacent to a nitrogen atom

Photoredox functionalization of C–H bonds adjacent to a nitrogen atom

Organic Photoredox Catalysis

Organic Reactions Promoted by Metal-Free Organic Dyes Under Visible Light Irradiation

Contact Info

Product

Resources

About