Tardiff, Bennett J. published the artcileRational and Predictable Chemoselective Synthesis of Oligoamines via Buchwald-Hartwig Amination of (Hetero)Aryl Chlorides Employing Mor-DalPhos, Product Details of C30H42NOP, the publication is Journal of Organic Chemistry (2012), 77(2), 1056-1071, database is CAplus and MEDLINE.
A diverse demonstration of synthetically useful chemoselectivity in the synthesis of di-, tri-, and tetraamines (62 examples) by use of Buchwald-Hartwig amination employing a single catalyst system ([Pd(cinnamyl)Cl]2/L1; L1 = N-(2-(di(1-adamantyl)phosphino)phenyl)morpholine, Mor-DalPhos) was reported. Competition reactions established the following relative preference of this catalyst system for amine coupling partners: linear primary alkylamines and imines > unhindered electron-rich primary anilines, primary hydrazones, N,N-dialkylhydrazines, and cyclic primary alkylamines > unhindered electron-deficient primary anilines, ¦Á-branched acyclic primary alkylamines, hindered electron-rich primary anilines ? cyclic and acyclic secondary dialkylamines, secondary alkyl/aryl and diarylamines, ¦Á,¦Á-branched primary alkylamines, and primary amides. The new isomeric ligand N-[4-[di(1-adamantyl)phosphino]phenyl]morpholine (p-Mor-DalPhos, L2) was prepared in 63% yield and was crystallog. characterized; the [Pd(cinnamyl)Cl]2/L2 catalyst system exhibited divergent reactivity. Application of the reactivity trends established for [Pd(cinnamyl)Cl]2/L1 toward the chemoselective synthesis of di-, tri-, and tetraamines was achieved. Preferential arylation was observed at the primary alkylamine position within 2-(4-aminophenyl)ethylamine with [Pd(cinnamyl)Cl]2/L1 and 4-chlorotoluene (affording I); the alternative regioisomer (II) was obtained when using [Pd(cinnamyl)Cl]2/L2. These observations are in keeping with coordination chem. studies, whereby binding of 2-(4-aminophenyl)ethylamine to the in situ generated [(L1)Pd(p-tolyl)]+ fragment occurred via the primary amine moiety, affording the crystallog. characterized adduct [(L1)Pd(p-tolyl)(NH2CH2CH2(4-C6H4NH2))]+OTf– in 72% yield.
Journal of Organic Chemistry published new progress about 1237588-12-3. 1237588-12-3 belongs to catalysis-chemistry, auxiliary class Mono-phosphine Ligands, name is 4-(2-(Di(adamantan-1-yl)phosphino)phenyl)morpholine, and the molecular formula is C13H13N5O, Product Details of C30H42NOP.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia