Proline catalyzes direct C-H arylations of unactivated arenes.

doi:10.1021/JO3008594

Paper

Proline catalyzes direct C-H arylations of unactivated arenes.

Published Aug 29, 2012 · Kouichi Tanimoro, M. Ueno, Kazutaka Takeda

The Journal of organic chemistry

Q2 SJR score

90

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0

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Abstract

Several amino acids were tested to catalyze the transition-metal-free direct C-H arylation of unactivated benzene derivatives. Among them, proline was found to be an excellent catalyst for the cross-coupling between aryl halides and unactivated arenes. The reaction presumably involves an aryl radical anion as the intermediate based on several experiments. The reaction using this catalyst system offers an option toward establishing an environmentally benign and cost-effective route to biaryls.

Highly Cited

Study Snapshot

Proline is an excellent catalyst for environmentally benign and cost-effective direct C-H arylation of unactivated arenes, offering an environmentally benign and cost-effective route to biaryls.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Proline catalyzes direct C-H arylations of unactivated arenes.

References

Citations

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Iodoarene activation offers eco-friendly, inexpensive, and functional group-tolerant green alternatives to transition metal-based catalysis for constructing functionalized (hetero)arenes under benign conditions.

K2CO3-Catalyzed Dual C-C-Coupled Cyclization to 3-Amino-4-benzoylbiphenyls and In Situ I2-Catalyzed C-N Bond Forming Annulation: A Metal-Free Synthesis of Arylacridones.

Metal-free cyclization catalysis reactions using K2CO3 and I2 enable the regioselective synthesis of 3-amino-4-benzoyl biphenyls and arylacridones with high atom economy.

Electrochemical synthesis of biaryls by reductive extrusion from N,N’-diarylureas

This electrochemical approach allows for the synthesis of various biaryls without transition-metal catalysts, offering complementary reactivity to metal catalyzed methods.

Short and Scalable Synthesis of Enantiopure N-Boc-trans-4-methyl-L-prolinol

A scalable, chromatography-free synthesis of enantiopure N-Boc-trans-4-methyl-L-prolinol using commercially available amino acids provides a promising building block for diverse 4-alkyl-L-prolines.

Sulfoxylate Anion Radical-Induced Aryl Radical Generation and Intramolecular Arylation for the Synthesis of Biarylsultams.

This study presents a green, practical, and efficient method for synthesis of diverse six- and seven-membered biarylsultams using sulfoxylate anion radicals and industrial reagents.