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 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.

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.

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...

Visible Light-Induced Sulfonylation/Arylation of Styrenes in a Double Radical Three-Component Photoredox Reaction

2019 ◽  
Author(s):  
Benjamin Lipp ◽  
Lisa Marie Kammer ◽  
Murat Kucukdisli ◽  
Adriana Luque ◽  
Jonas Kühlborn ◽  
...  
Keyword(s):  
Visible Light ◽  
Radical Formation ◽  
Three Component Reaction ◽  
Broad Variety ◽  
Styrene Derivatives ◽  
Mechanistic Investigations

Simultaneous sulfonylation/arylation of styrene derivatives is achieved in a photoredox-catalyzed three-component reaction using visible light. A broad variety of difunctionalized products is accessible in mostly excellent yields and high diastereoselectivity. The developed reaction is scalable and suitable for the modification of styrene-functionalized biomolecules. Mechanistic investigations suggest the transformation to be operating through a designed sequence of radical formation and radical combination.<br>

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.

Rh(III)-Catalyzed Olefination and Alkylation of Arenes with Maleimides: A Tunable Strategy for C(sp2)–H Functionalization

Synthesis ◽  
2021 ◽  
Author(s):  
Hongji Li ◽  
Wenjie Zhang ◽  
Xueyan Liu ◽  
Zhenfeng Tian
Keyword(s):  
Room Temperature ◽  
Functional Group ◽  
Reaction Conditions ◽  
Bond Functionalization ◽  
Alkylation Process ◽  
Coupling Partner

AbstractWe herein report a new nitrogen-directed Rh(III)-catalyzed C(sp2)–H bond functionalization of N-nitrosoanilines and azoxybenzenes with maleimides as a coupling partner, in which the olefination/alkylation process can be finely controlled at room temperature by variation of the reaction conditions. This method shows excellent functional group tolerance, and presents a mild access to the resulting olefination/alkylation products in moderate to good yields.

Azulene as an ingredient for visible-light- and stimuli-responsive photoswitches

2021 ◽  
Author(s):  
Andrey G. Lvov ◽  
Aleksei Bredihhin
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Unique Combination ◽  
Stimuli Responsive

The azulene molecule features an unique combination of optical, luminescent, and stimuli-responsive properties. This makes the azulene motif a promising functional group to be introduced in photoswitches. Recent challenges in...

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