2012
DOI: 10.1002/ejoc.201201241
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Tsuji–Trost N‐Allylation with Allylic Acetates by Using a Cellulose–Palladium Catalyst

Abstract: Allylic amines were synthesized by a simple procedure using a biodegradable and easily recyclable heterogeneous cellulose–Pd catalyst through N‐allylation of primary and secondary amines. The scope of this protocol includes aliphatic and benzylamines with substituted and unsubstituted allyl acetates and culminates in high yield syntheses. The highlights of the protocol include a ligand‐free reaction, simple workup, and catalyst recyclability.

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Cited by 26 publications
(15 citation statements)
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“…This chelation mechanism is likely in view of the literature, for example, reporting a Pd-immobilized cellulose. 15 We envisioned that the addition of a reagent capable of capturing K + ions might be effective for the dissolution of cellulose even in the presence of K + ions. We selected 18-crown-6 (18C6), known as an excellent ligand for K + (Fig.…”
mentioning
confidence: 99%
“…This chelation mechanism is likely in view of the literature, for example, reporting a Pd-immobilized cellulose. 15 We envisioned that the addition of a reagent capable of capturing K + ions might be effective for the dissolution of cellulose even in the presence of K + ions. We selected 18-crown-6 (18C6), known as an excellent ligand for K + (Fig.…”
mentioning
confidence: 99%
“…Much effort has been made toward the synthesis of thiocyanates so far. Generally, thiocyanates can be synthesized via the following two major routes (Scheme 1(a)): (1) thiocyanation of organic partners (arenes, organic halides, diazonium salts, and arylboronic acids) in the presence of inorganic thiocyanates 1015 and (2) cyanation of organosulfur compounds including thiols, disulfides, and sulfinates with electrophilic and nucleophilic cyanation reagents. 1620 Thiocyanates can also be prepared via CuCN-mediated direct aerobic oxidative cyanation of thiophenols and diaryl disulfides.…”
Section: Introductionmentioning
confidence: 99%
“…In light of this, we have reported highly efficient catalysts for Suzuki–Miyaura couplings based on immobilization of Pd NPs on cellulose or carboxymethylcellulose in our previous work. Sodium carboxymethylcellulose (CMC–Na) carrying a tremendous number of carboxymethyl groups (−CH 2 –COO − Na + ) has excellent cation exchange capacity . Considering this characteristic, CMC–Na has been reported to serve as a template for the preparation of magnetic Fe 3 O 4 organic/inorganic hybrid.…”
Section: Introductionmentioning
confidence: 99%