19788-35-3Relevant articles and documents
Auxiliary-Directed Pd-Catalyzed γ-C(sp3)-H Bond Activation of α-Aminobutanoic Acid Derivatives
Pasunooti, Kalyan Kumar,Banerjee, Biplab,Yap, Terence,Jiang, Yaojia,Liu, Chuan-Fa
, p. 6094 - 6097 (2015)
New bidentate auxiliaries derived from the isoxazole-3-carboxamide and oxazole-4-carboxamide moieties were used for Pd-catalyzed C(sp3)-H bond activation. The results show that, when placed on a primary amine compound, 5-methylisoxazole-3-carboxamide (MICA) directs Pd-catalyzed activation of inert γ-C(sp3)-H bonds for C-C bond formation. Selective and efficient arylation and alkylation of several α-aminobutanoic acid derivatives led to various γ-substituted non-natural amino acids. The MICA directing group can be conveniently removed and recovered under very mild conditions.
Two-step cyanomethylation protocol: Convenient access to functionalized aryl- and heteroarylacetonitriles
Lindsay-Scott, Peter J.,Clarke, Aimee,Richardson, Jeffery
supporting information, p. 476 - 479 (2015/03/05)
A two-step protocol has been developed for the introduction of cyanomethylene groups to metalated aromatics through the intermediacy of substituted isoxazoles. A palladium-mediated cross-coupling reaction was used to introduce the isoxazole unit, followed by release of the cyanomethylene function under thermal or microwave-assisted conditions. The intermediate isoxazoles were shown to be amenable to further functionalization prior to deprotection of the sensitive cyanomethylene motif, allowing access to a wide range of aryl- and heteroaryl-substituted acetonitrile building blocks.
