Iterative Arylation of Amino Acids and Aliphatic Amines via δ‐C(sp 3 )−H Activation: Experimental and Computational Exploration

Autor:	Sukumar Pradhan, Robert S. Paton, Vikas Kumar Singh, Xinglong Zhang, Satyadip Paul, Srimanta Guin, Debabrata Maiti, Hediyala B. Chandrashekar, S. S. Anjana, Pravas Dolui
Rok vydání:	2019
Předmět:	chemistry.chemical_classification 010405 organic chemistry Chemistry Substrate (chemistry) General Chemistry General Medicine 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences Amino acid chemistry.chemical_compound Organopalladium Surface modification Reactivity (chemistry)
Zdroj:	Angewandte Chemie. 131:5689-5694
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.201900479
Popis:	Directed C-H functionalization has been realized as a complementary tool to the traditional approaches for a straightforward access of non-proteinogenic amino acids; albeit such a process is restricted mostly up to the γ-position. In the present work, we demonstrate the diversification [(hetero)arylation] of amino acids and analogous aliphatic amines selectively at the remote δ-position by tuning the reactivity controlled by ligands. An organopalladium δ-C(sp3)-H activated intermediate has been isolated and crystallographically characterized. Mechanistic investigations carried out experimentally in conjunction with computational studies shed light on the difference in the mechanistic picture depending on the substrate structure.
Databáze:	OpenAIRE
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