2013
DOI: 10.1002/adsc.201300317
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N‐Benzylation/Benzylic CH Amidation Cascade by the (η3‐Benzyl)palladium System in Aqueous Media: An Effective Pathway for the Direct Construction of 3‐Phenyl‐3,4‐dihydro‐ (2H)‐1,2,4‐benzothiadiazine 1,1‐Dioxides

Abstract: We demonstrate a unique strategy for a benzylation/benzylic C À H amidation cascade reaction by the (h 3

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Cited by 30 publications
(12 citation statements)
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“…The borrowing hydrogen methodology involves (1) oxidation of alcohols or ammonia to the corresponding carbonyl compounds or imines; (2) alkylation of ketones, alcohols, or amines to form unsaturated carbonyl compounds or imines; and (3) reduction of the C–C or C–N bonds using the borrow hydrogen atoms from alcohols or amines (Scheme ). , Generally, among these transformations, the catalyst plays a crucial role in every step. To date, although some metals (Pd, Au, Ag, Cu, Fe, Ni, Os, and Rh,) have been studied, Ru and Ir are still shown to be the most effective and promising catalysts for C-alkylation and N-alkylation.…”
Section: Introductionmentioning
confidence: 99%
“…The borrowing hydrogen methodology involves (1) oxidation of alcohols or ammonia to the corresponding carbonyl compounds or imines; (2) alkylation of ketones, alcohols, or amines to form unsaturated carbonyl compounds or imines; and (3) reduction of the C–C or C–N bonds using the borrow hydrogen atoms from alcohols or amines (Scheme ). , Generally, among these transformations, the catalyst plays a crucial role in every step. To date, although some metals (Pd, Au, Ag, Cu, Fe, Ni, Os, and Rh,) have been studied, Ru and Ir are still shown to be the most effective and promising catalysts for C-alkylation and N-alkylation.…”
Section: Introductionmentioning
confidence: 99%
“…18 Very recently, a Pd-catalyzed synthetic route was developed for the preparation of benzothiadiazine derivatives by using o-aminobenzene-sulfonamide and primary alcohols as starting materials. 19 Generally, these compounds were prepared from o-amino-benzenesulfonamide by condensation with aldehydes or ethyl hemiacetals in acidic medium. 20 As shown in Table 4, using the present system, the nal products, cyclic aminals (7) without C]N bond formation were obtained.…”
Section: Resultsmentioning
confidence: 99%
“…We have been developing environmentally benign benzylic CÀ H functionalizations at sites adjacent to heteroatoms utilizing the π-benzylpalladium system in water. [9] The catalytic amination of CÀ H bonds is recognized as an atom-economic, straightforward and efficient method that can incorporate nitrogen into molecular frameworks without pre-activation of starting materials. [10] Herein, we present the first example of the direct use of benzylic alcohols for MCR of isatoic anhydrides with amines catalyzed by Pd(0)/ TPPMS in water, furnishing a series of 2-aryl quinazolinone derivatives (Scheme 1C).…”
Section: Updatesmentioning
confidence: 99%