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Ruthenium‐Catalyzed Three‐Component Alkylation: A Tandem Approach to the Synthesis of Nonsymmetric N,N‐ Dialkyl Acyl Hydrazides with Alcohols
Author(s) -
Bettoni Léo,
Joly Nicolas,
Lohier JeanFrançois,
Gaillard Sylvain,
Poater Albert,
Renaud JeanLuc
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100554
Subject(s) - chemistry , tandem , ruthenium , aldehyde , catalysis , alkylation , ketone , methanol , alcohol , organic chemistry , primary (astronomy) , cascade reaction , phosphine , combinatorial chemistry , materials science , physics , astronomy , composite material
The borrowing hydrogen strategy has been applied in the synthesis of nonsymmetric N , N ‐dialkylated acyl hydrazides via a tandem three‐component reaction catalyzed by a phosphine free diaminocyclopentadienone ruthenium tricarbonyl complex. This strategy represents the first direct one‐pot approach to nonsymmetric functionalized acyl hydrazides. Different aromatic acyl hydrazides underwent dialkylation with a variety of primary or secondary alcohols and methanol or ethanol as alkylating agents in mild reaction conditions and good yields. Deuterium labelling experiments suggested that the primary or secondary alcohol was the hydrogen source in this tandem process. DFT calculations show that the combination of the tandem mixed product cannot be perfectly explained neither structurally nor electronically, but might be dependent of the physical state of the aldehyde or ketone intermediate (gaz vs. liquid) at the reaction temperature.