Metal-free visible-light-induced photoredox-catalyzed intermolecular pyridylation/phosphinoylation of alkenes

Author(s): Jiaxuan Shen ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Yipin Zhang ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Yanjiang Yu ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Manman Wang ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵

Publication date (Electronic): 2021

Journal: Organic Chemistry Frontiers

Publisher: Royal Society of Chemistry (RSC)

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Abstract

A visible-light-induced and photoredox-catalyzed intermolecular pyridylation/phosphinoylation of alkenes using 4-cyanopyridine and diphenylphosphine oxide under mild metal-free conditions has been reported.

Abstract

Reported here is an intermolecular pyridylation/phosphinoylation of alkenes using 4-cyanopyridine and diphenylphosphine oxide under visible-light-induced organic photoredox catalysis. The reaction occurs under mild metal-free conditions, possessing a broad substrate scope. The protocol can be practiced on a gram scale and applied to the modification of natural product-derived and medicinally relevant complex molecules containing a styrene unit. Mechanistic investigations suggest that triethylamine serves as both single-electron transfer (SET) and hydrogen atom transfer (HAT) agents.

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Organic Photoredox Catalysis.

Nathan Romero, David Nicewicz (2016)

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.

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Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals.

Edon Vitaku, David Smith, Jon Njardarson (2014)

Nitrogen heterocycles are among the most significant structural components of pharmaceuticals. Analysis of our database of U.S. FDA approved drugs reveals that 59% of unique small-molecule drugs contain a nitrogen heterocycle. In this review we report on the top 25 most commonly utilized nitrogen heterocycles found in pharmaceuticals. The main part of our analysis is divided into seven sections: (1) three- and four-membered heterocycles, (2) five-, (3) six-, and (4) seven- and eight-membered heterocycles, as well as (5) fused, (6) bridged bicyclic, and (7) macrocyclic nitrogen heterocycles. Each section reveals the top nitrogen heterocyclic structures and their relative impact for that ring type. For the most commonly used nitrogen heterocycles, we report detailed substitution patterns, highlight common architectural cores, and discuss unusual or rare structures.