Tetrazole-Fragmentation for the Generation of Alkylidene Carbenes from Cyanophosphates under Neutral Conditions and Its Application to Organic Synthesis

Shinya Harusawa; Hiroki Yoneyama

doi:10.3987/rev-18-894

Tetrazole-Fragmentation for the Generation of Alkylidene Carbenes from Cyanophosphates under Neutral Conditions and Its Application to Organic Synthesis

Heterocycles ◽

10.3987/rev-18-894 ◽

2018 ◽

Vol 96 (12) ◽

pp. 2037 ◽

Cited By ~ 5

Author(s):

Shinya Harusawa ◽

Hiroki Yoneyama

Keyword(s):

Organic Synthesis ◽

Neutral Conditions ◽

Alkylidene Carbenes

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Ruthenium catalysis in organic synthesis

Pure and Applied Chemistry ◽

10.1351/pac200274010019 ◽

2002 ◽

Vol 74 (1) ◽

pp. 19-24 ◽

Cited By ~ 48

Author(s):

Shun-Ichi Murahashi ◽

Hikaru Takaya ◽

Takeshi Naota

Keyword(s):

Organic Synthesis ◽

Lewis Acid ◽

Catalytic Reactions ◽

Biologically Active ◽

Hydride Complexes ◽

Base Catalysts ◽

Acid And Base ◽

Ruthenium Catalysis ◽

Lewis Acid And Base ◽

Neutral Conditions

Ruthenium, rhodium, iridium, and rhenium hydride complexes are highly useful redox Lewis acid and base catalysts. Various substrates bearing hetero atoms are activated by these catalysts and undergo reactions with either nucleophiles or electrophiles under neutral conditions. These types of catalytic reactions are described together with their application to the preparation of various biologically active compounds.

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Photo-induced catalytic halopyridylation of alkenes

Nature Communications ◽

10.1038/s41467-021-26857-w ◽

2021 ◽

Vol 12 (1) ◽

Author(s):

Shi-Yu Guo ◽

Fan Yang ◽

Ting-Ting Song ◽

Yu-Qing Guan ◽

Xiang-Ting Min ◽

...

Keyword(s):

Organic Synthesis ◽

Heck Reaction ◽

Cross Coupling ◽

Photoredox Catalysis ◽

Radical Process ◽

Type Reaction ◽

Plausible Mechanism ◽

Mechanistic Investigations ◽

Neutral Conditions

AbstractThe Mizoroki-Heck reaction and its reductive analogue are staples of organic synthesis, but the ensuing products often lack a chemical handle for further transformation. Here we report an atom-economical cross-coupling of halopyridines and unactivated alkenes under photoredox catalysis to afford a series of alkene halopyridylation products. This protocol with mild and redox neutral conditions contributes broad substrate scope. As a complement to conventional Heck-type reaction, this radical process avoids the involvement of β-H elimination and thus useful pyridyl and halide groups could be simultaneously and regioselectively incorporated onto alkenes. The success depends on TFA-promoted domino photocatalytic oxidative quenching activation and radical-polar crossover pathway. Plausible mechanism is proposed based on mechanistic investigations. Moreover, the reserved C − X bonds of these products are beneficial for performing further synthetic elaborations.

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