Visible-Light-Driven Phosphonoalkylation of Alkenes

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.

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Photocatalytic Synthesis of Tetra-Substituted Furans Promoted by Carbon Dioxide

Chemical Science ◽

10.1039/d1sc06403g ◽

2021 ◽

Author(s):

Ya-Ming Tian ◽

Huaiju Wang ◽

Ritu Ritu ◽

Burkhard Koenig

Keyword(s):

Carbon Dioxide ◽

Transition Metal ◽

Visible Light ◽

Metal Free ◽

Mild Conditions ◽

Simple Protocol ◽

Visible Light Driven ◽

Substituted Furans ◽

Photocatalytic Synthesis

We report a simple protocol for the transition metal-free, visible-light-driven conversion of 1,3-diketones to tetra-substituted furan skeleton compounds in carbon dioxide (CO2) atmosphere under mild conditions. It was found that...

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Metal free visible light driven oxidation of alcohols to carbonyl derivatives using 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) as catalyst

RSC Advances ◽

10.1039/c5ra18151h ◽

2015 ◽

Vol 5 (102) ◽

pp. 84328-84333 ◽

Cited By ~ 13

Author(s):

Suvendu Samanta ◽

Papu Biswas

Keyword(s):

Visible Light ◽

Visible Light Irradiation ◽

Room Temperature ◽

Light Irradiation ◽

Metal Free ◽

Carbonyl Derivatives ◽

Oxidation Of Alcohols ◽

Visible Light Driven ◽

High Yields

A metal-free transformation of alcohols to the corresponding carbonyls in high yields under visible-light irradiation has been achieved at room temperature using di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) as catalyst.

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

10.21203/rs.3.rs-93319/v1 ◽

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.

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Transition-Metal-Free Synthesis of Phenanthridinones through Visible-Light-Driven Oxidative C-H Amidation

European Journal of Organic Chemistry ◽

10.1002/ejoc.201900536 ◽

2019 ◽

Vol 2020 (10) ◽

pp. 1496-1504 ◽

Cited By ~ 3

Author(s):

Kaoru Usami ◽

Eiji Yamaguchi ◽

Norihiro Tada ◽

Akichika Itoh

Keyword(s):

Transition Metal ◽

Visible Light ◽

Metal Free ◽

Visible Light Driven

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ChemInform Abstract: Transition Metal-Free Visible Light-Driven Photoredox Oxidative Annulation of Arylamidines.

ChemInform ◽

10.1002/chin.201620175 ◽

2016 ◽

Vol 47 (20) ◽

Author(s):

Zi-chao Shen ◽

Pan Yang ◽

Yu Tang

Keyword(s):

Transition Metal ◽

Visible Light ◽

Metal Free ◽

Visible Light Driven

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Visible-light-promoted selective C–H amination of heteroarenes with heteroaromatic amines under metal-free conditions

Organic & Biomolecular Chemistry ◽

10.1039/c7ob02504a ◽

2017 ◽

Vol 15 (45) ◽

pp. 9590-9594 ◽

Cited By ~ 26

Author(s):

Supravat Samanta ◽

Chitrakar Ravi ◽

Sadu Nageswara Rao ◽

Abhisek Joshi ◽

Subbarayappa Adimurthy

Keyword(s):

Transition Metal ◽

Visible Light ◽

Room Temperature ◽

Functional Group ◽

Metal Free ◽

High Degree

The regioselective C–H amination of quinoline amides (C5) and imidazopyridines (C3) under transition-metal-free conditions at room temperature with a high degree of functional group tolerance is reported.

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Transition-Metal-Free Synthesis of Trifluoromethylated Furans via a Bu3P-Mediated Tandem Acylation–Wittig Reaction

Synlett ◽

10.1055/s-0040-1707263 ◽

2020 ◽

Vol 31 (20) ◽

pp. 2035-2038

Author(s):

Wei Zhou ◽

Maizhan Li

Keyword(s):

Transition Metal ◽

Functional Groups ◽

Nucleophilic Addition ◽

Wittig Reaction ◽

Reaction Conditions ◽

Metal Free ◽

Highly Efficient ◽

Intramolecular Wittig Reaction ◽

High Yields

AbstractA highly efficient nucleophilic addition–O-acylation–intramolecular Wittig reaction of β-trifluoromethyl α,β-enones is disclosed. This strategy features mild reaction conditions and provides a practical transition-metal-free method to a set of biologically significant trifluoromethylated furans in high yields with diverse functional groups.

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Transition-Metal-Free Synthesis of Thiosulfonates through Radical Coupling Reaction

Synlett ◽

10.1055/s-0037-1610649 ◽

2018 ◽

Vol 29 (15) ◽

pp. 2076-2080 ◽

Cited By ~ 4

Author(s):

Wen-Ting Wei ◽

Zhiyong Guo ◽

Guodong Zhou ◽

Xu-Dong Xu ◽

Gan-Ping Chen

Keyword(s):

Transition Metal ◽

Coupling Reaction ◽

Cross Coupling ◽

Mechanistic Studies ◽

Reaction Conditions ◽

Coupling Process ◽

Metal Free ◽

Radical Coupling ◽

Radical Coupling Reaction ◽

High Yields

An efficient and practical transition-metal-free radical coupling reaction of sulfonyl hydrazides mediated by NIS/K2S2O8 has been developed to afford a variety of biological activity thiosulfonates in moderate to excellent yields. Compared to a known approach for the synthesis of thiosulfonates from sulfonyl hydrazides, this strategy features high yields, mild reaction conditions, and broad substrate scope. The mechanistic studies revealed that the procedure undergoes via a radical cross-coupling process for the construction of S–S bonds.

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