scholarly journals Direct sulfonylation of anilines mediated by visible light

2018 ◽  
Vol 9 (3) ◽  
pp. 629-633 ◽  
Author(s):  
Tarn C. Johnson ◽  
Bryony L. Elbert ◽  
Alistair J. M. Farley ◽  
Timothy W. Gorman ◽  
Christophe Genicot ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Visible Light Photocatalysis ◽  
Reaction Conditions

Visible light photocatalysis allows the introduction of the sulfone functional group to anilines under mild reaction conditions, without the need for pre-functionalization.

Visible-light-induced anti-Markovnikov hydrosulfonation of styrene derivatives

2020 ◽  
Vol 7 (15) ◽  
pp. 2069-2074 ◽  
Author(s):  
Yinan Zheng ◽  
Ying You ◽  
Qianqian Shen ◽  
Junjie Zhang ◽  
Le Liu ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Reaction Conditions ◽  
Styrene Derivatives

A visible-light-induced anti-Morkovnikov hydrosulfonation reaction of styrene derivatives with sodium sulfinates has been developed, featuring mild reaction conditions, good functional-group tolerance, good yields and high regioselectivity.

scholarly journals Tyrosine and Drug-like Late-stage Benzylic Functionalization via Photoredox Catalysis

2020 ◽  
Author(s):  
Tobias Brandhofer ◽  
Volker Derdau ◽  
María Mendez ◽  
Christoph Pöverlein ◽  
Olga Garcia Mancheno
Keyword(s):  
Natural Products ◽  
Visible Light ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Functional Group ◽  
Reaction Conditions ◽  
Site Selectivity ◽  
Wide Range ◽  
High Yields ◽  
Therapeutic Compounds

Abstract Visible light mediated late-stage functionalization is a rising field in synthetic and medicinal chemistry, allowing the fast and diversified modification of valuable, potentially therapeutic compounds such as peptides. However, there are relatively few mild methodologies for the C(sp3)-H functionalization of complex peptides. Herein, we report a visible light mediated photocatalytic protocol for the benzylic C-H modification of tyrosine and related C-H bonds. The embraced radical-cation/deprotonation strategy enables an incorporation of a wide range of valuable functional groups in high yields and chemoselectivity. The mild reaction conditions, site-selectivity and high functional group tolerance was highlighted by the functionalization of complex peptides, drugs and natural products, providing a promising synthetic platform in medicinal chemistry.

scholarly journals Visible light photoredox-catalyzed deoxygenation of alcohols

2014 ◽  
Vol 10 ◽  
pp. 2157-2165 ◽  
Author(s):  
Daniel Rackl ◽  
Viktor Kais ◽  
Peter Kreitmeier ◽  
Oliver Reiser
Keyword(s):  
Natural Products ◽  
Visible Light ◽  
Blue Light ◽  
Functional Group ◽  
Bond Cleavage ◽  
Environmentally Benign ◽  
Visible Light Photocatalysis ◽  
Water Mixture ◽  
Visible Light Photocatalyst ◽  
Single Bonds

Carbon–oxygen single bonds are ubiquitous in natural products whereas efficient methods for their reductive defunctionalization are rare. In this work an environmentally benign protocol for the activation of carbon–oxygen single bonds of alcohols towards a reductive bond cleavage under visible light photocatalysis was developed. Alcohols were activated as 3,5-bis(trifluoromethyl)-substituted benzoates and irradiation with blue light in the presence of [Ir(ppy)2(dtb-bpy)](PF6) as visible light photocatalyst and Hünig’s base as sacrificial electron donor in an acetonitrile/water mixture generally gave good to excellent yields of the desired defunctionalized compounds. Functional group tolerance is high but the protocol developed is limited to benzylic, α-carbonyl, and α-cyanoalcohols; with other alcohols a slow partial C–F bond reduction in the 3,5-bis(trifluoromethyl)benzoate moiety occurs.

scholarly journals The A3 Redox-Neutral C1-Alkynylation of Tetrahydroisoquinolines: A Comparative Study between Visible Light Photocatalysis and Transition-Metal Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Vladimir V. Kouznetsov ◽  
Marlyn C. Ortiz Villamizar ◽  
Carlos E. Puerto Galvis
Keyword(s):  
Transition Metal ◽  
Microwave Irradiation ◽  
Visible Light ◽  
High Selectivity ◽  
Transition Metal Catalysis ◽  
Visible Light Photocatalysis ◽  
Reaction Conditions ◽  
Metal Catalysis ◽  
New Compounds ◽  
Optimal Reaction

AbstractConsidering the current challenges of the A3 redox-neutral C1-alkynylation of tetrahydroisoquinolines (THIQs), we studied this synthetic tool under visible light photocatalysis and transition-metal catalysis in order to describe alternative reaction conditions and discuss possible improvements to this process. We demonstrated that 1-alkynylated THIQs can be readily obtained by three different approaches: iridium-based photocatalysis and copper ([CuBr(PPh3)3]) and silver (AgNO3) catalysis under mild, selective and accessible reaction conditions. Among these approaches, the copper(I)-based methodology resulted in the most robust, optimal reaction conditions for the synthesis of a series of 18 1-alkynylated THIQs in moderate to excellent yields and with high selectivity for the endo-alkynylated products. Moreover, this reaction can be accelerated by microwave irradiation (120 °C, 15 min) affording a novel library of diverse THIQs with alkyne and N-substituent moieties, from unreactive and uncommon substrates, that could be further transformed into new compounds of interest.

Visible-Light-Driven Phosphonoalkylation of Alkenes

Synlett ◽  
2021 ◽  
Vol 32 (04) ◽  
pp. 378-382
Author(s):  
Yue-Ming Jiang ◽  
Jie Liu ◽  
Qiang Fu ◽  
Yu-Ming Yu ◽  
Da-Gang Yu
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Functional Group ◽  
Reaction Conditions ◽  
Metal Free ◽  
Alkyl Sulfonates ◽  
Visible Light Driven ◽  
High Yields

AbstractPhosphonylation of alkenes is important for the generation of valuable organophosphines. However, redox-neutral difunctionalization of alkenes with readily available H-P(O) compounds remains underdeveloped. Herein, we report the first visible-light-driven redox-neutral phosphonoalkylation of alkenes. A variety of organophosphorus-containing three-membered carbocyclic scaffolds are synthesized from alkene-bearing alkyl sulfonates with H-P(O) compounds. The transition-metal-free protocol displays good functional group tolerance, broad substrate scope, high yields, and mild reaction conditions.

Visible-Light Photocatalytic Ugi/Aza-Wittig Cascade Towards 2-aminomethyl-1,3,4-oxadiazole derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Camilla Russo ◽  
Rolando Cannalire ◽  
Paolo Luciano ◽  
Francesca Brunelli ◽  
Giancesare Tron ◽  
...  
Keyword(s):  
Amino Acids ◽  
Visible Light ◽  
Multicomponent Reaction ◽  
Late Stage ◽  
Functional Group ◽  
Synthetic Approach ◽  
Reaction Conditions ◽  
One Pot ◽  
Oxadiazole Derivatives ◽  
Visible Light Photocatalytic

A new visible light photocatalytic multicomponent reaction (MCR) involving N-alkyl-N-methylanilines, N-isocyanoiminotriphenyl phosphorane, and carboxylic acids leading to 1,3,4-oxadiazole derivatives is herein reported. The developed mild reaction conditions enable a broad substrate scope and a good functional group tolerance, as further highlighted in the late stage functionalization of amino acids and drugs. Additionally, a 2-step one-pot protocol for the obtention of non-symmetrical diacylhydrazines is also reported as an expeditious and green synthetic approach to such valuable scaffolds.

Visible-light-induced tandem radical addition/cyclization of 2-alkenylphenols and CBr4 for synthesis of 4-arylcoumarins

2021 ◽  
Author(s):  
Li-Ping Tan ◽  
Dong Liang ◽  
Ying Cheng ◽  
Wen-Jing Xiao ◽  
Jia-Rong Chen
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Radical Addition ◽  
Reaction Conditions ◽  
Neutral Reaction ◽  
Operational Simplicity

A visible-light-induced photoredox-catalyzed tandem radical addition/cyclization of 2-alkenylphenols and CBr4 is developed. This protocol features mild and redox-neutral reaction conditions, good functional-group tolerance, and operational simplicity, providing efficient and practical...

Rhodamines as Photocatalyst in Organic Synthesis

2020 ◽  
Vol 07 ◽  
Author(s):  
Avik K. Bagdi ◽  
Papiya Sikdar
Keyword(s):  
Visible Light ◽  
Organic Synthesis ◽  
Organic Dyes ◽  
Transition Metal Catalysts ◽  
Visible Light Photocatalysis ◽  
Eosin Y ◽  
Organic Transformations ◽  
The Sustainable Development ◽  
Mechanistic Pathway ◽  
Green Model

Abstract:: Organic synthesis under environment friendly conditions has great impact in the sustainable development. In this context, visible light photocatalysis has emerged as a green model as this offers an energy-efficient pathway towards the organic transformation. Different transition-metal catalysts (Ir-, Ru-, Cu- etc) and organic dyes (eosin Y, rose bengal, methylene blue etc) are well-known photocatalysts in organic synthesis. Apart from the well-known organophotoredox catalysts, rhodamines (Rhodamine B and Rhodamine 6G) have been also employed as efficient photocatalysts for different organic transformations. In this review, we will focus on the photocatalysis by rhodamines in organic synthesis. Mechanistic pathway of the methodologies will also be discussed. We believe this review will stimulate the employment of rhodamines in the visible light photocatalysis for efficient organic transformations in the future.

Modern Organic Synthesis in the Laboratory

2008 ◽  
Author(s):  
Jie Jack Li ◽  
Chris Limberakis ◽  
Derek A. Pflum
Keyword(s):  
Organic Chemistry ◽  
Graduate Students ◽  
Organic Synthesis ◽  
Functional Group ◽  
Bond Formation ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Oxidation Reduction ◽  
Carbon Carbon Bond ◽  
Daunting Task

Searching for reaction in organic synthesis has been made much easier in the current age of computer databases. However, the dilemma now is which procedure one selects among the ocean of choices. Especially for novices in the laboratory, it becomes a daunting task to decide what reaction conditions to experiment with first in order to have the best chance of success. This collection intends to serve as an "older and wiser lab-mate" one could have by compiling many of the most commonly used experimental procedures in organic synthesis. With chapters that cover such topics as functional group manipulations, oxidation, reduction, and carbon-carbon bond formation, Modern Organic Synthesis in the Laboratory will be useful for both graduate students and professors in organic chemistry and medicinal chemists in the pharmaceutical and agrochemical industries.

Nickel-Catalyzed Multicomponent Coupling Reaction of Alkyl Halides, Isocyanides and H2O: An Expedient Way to Access Alkyl Amides

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3466-3472
Author(s):  
Yunkui Liu ◽  
Bingwei Zhou ◽  
Qiao Li ◽  
Hongwei Jin
Keyword(s):  
Functional Group ◽  
Coupling Reaction ◽  
Alkyl Halides ◽  
Previous Literature ◽  
Catalytic Cycle ◽  
Reaction Conditions ◽  
Multicomponent Coupling ◽  
Easy Operation

We herein describe a Ni-catalyzed multicomponent coupling reaction of alkyl halides, isocyanides, and H2O to access alkyl amides. Bench-stable NiCl2(dppp) is competent to initiate this transformation under mild reaction conditions, thus allowing easy operation and adding practical value. Substrate scope studies revealed a broad functional group tolerance and generality of primary and secondary alkyl halides in this protocol. A plausible catalytic cycle via a SET process is proposed based on preliminary experiments and previous literature.

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