We report a Pd(II)-catalyzed bidentate directing group 8-aminoquinoline-aided, site-selective β-C-H functionalization protocol for assembling modified azobenzene carboxamides. Considering the importance of azobenzenes in chemical sciences, this paper reports a new...
Systematic investigations of a Pd(II)-catalyzed, 8aminoquinoline directing group (DG)-aided sp 2 δ-CÀ H amidation (CÀ N bond formation) of different biaryl carboxamides are reported. Various biaryl carboxamides with suitably positioned sp 2 δ-CÀ H bond with respect to the DG were assembled via β-CÀ H arylation and then they were subjected to Pd(II)-catalyzed sp 2 δ-CÀ H intramolecular amidation/annulation reactions. While the intramolecular amidation of the sp 2 δ-CÀ H bond of some carboxamides was not fruitful, several biaryl carboxamides underwent intramolecular amidation of their sp 2 δ-CÀ H bonds to afford various tricyclic quinolone motifs such as, phenanthridin-6(5H)-ones and thieno-/furo-/pyrrolo-[2,3-c]quinolin-4(5H)-ones. The assembly of the required biaryl carboxamides possessing the sp 2 δ-CÀ H bond via the β-CÀ H arylation and the successive intramolecular amidation (CÀ N bond formation) of the resulting biaryl carboxamides were also performed in one-pot reaction conditions to afford tricyclic quinolones. . Directing group-aided site-selective CÀ H activation. Scheme 2. Intramolecular amidation of the remote CÀ H bonds. . Assembling of 12 a-j suitably positioned with the sp 2 δ-CÀ H bond via the AQ-aided β-CÀ H arylation. Scheme 9. The Pd[II]-catalyzed, AQ-aided intramolecular amidation of 12 a-j.
This paper reports the synthesis of enantiopure aryl alkyl ethers via the Pd(II)-catalyzed picolinamide-aided γ-C(sp 2 )À H alkoxylation of various enantiopure α-alkylbenzylamine derivatives using alcohols. Enantiopure α-methylbenzylamines and amino alcohol substrates such as 2amino-2-phenylethanol (phenylglycinol) and 3-amino-3-phenylpropanol were subjected to the γ-C(sp 2 )À H alkoxylation (etherification) with alcohols using PIDA. α-Alkylbenzylamines and phenylglycinols are valuable building blocks in organic synthesis and medicinal chemistry research areas. Accordingly, this work has enabled the assembling of various enantiopure ortho-alkoxylated α-methylbenzylamine and 2-amino-2-phenylethanol (phenylglycinol) and 3-amino-3-phenylpropanol derivatives containing aryl alkyl ether functionality. We have shown the utility of ortho-alkoxylated αmethylbenzylamine derivatives for assembling enantiopure α-methylbenzylamine-based sulfamoylcarbamates and carboxamides which are structurally related to the bio-active compounds known in the literature. This work demonstrates the substrate scope elaboration in CÀ H functionalization and etherification through the CÀ O bond-forming process and synthesis of aryl alkyl ether functionality containing enantiopure α-alkylbenzylamines.
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