Fluorinated alcohol mediated N,N'-dialkylation of amino acid derivatives via cascade [1,5]-hydride transfer/cyclization for concise synthesis of tetrahydroquinazoline.

Structurally diverse amino acids and their ester derivatives were conveniently N,N'-dialkylated via a TFE-promoted cascade condensation/[1,5]-hydride transfer/cyclization for straightforward construction of pharmeutically significant tetrahydroquinazolines incorporating various amino acids, which featured broad substrate scope, the use of TFE as a sole solvent, additive-free and mild conditions.

Catalytic Formal Benzylic C-H Bond Functionalization of 2,5-Dialkylfuran Derivatives with Ferrocenyl Alcohols as Alkylation Reagents.

The inert benzylic C-H bond of π-electron-rich heteroaromatic 2,5-dialkylfuran derivatives was conveniently functionalized with ferrocenyl alcohols as alkylation reagents under catalytic acidic conditions at room temperature, which features chemo- and regiospecificity, mild and metallic catalyst-free conditions, and environmental benignity.

Redox-triggered cascade dearomative cyclizations enabled by hexafluoroisopropanol.

An unprecedented cascade dearomative cyclization through hydrogen-bonding-assisted hydride transfer is realized. The aggregate effect of HFIP enables the rapid buildup of polycyclic amines directly from phenols and o-aminobenzaldehydes via a cascade dearomatization/rearomatization/dearomatization sequence. This unique transformation addressed the drawbacks of hydride transfer-involved redox-neutral reactions.

SN1-Type Alkylation of N-Heteroaromatics with Alcohols.

The organocatalytic alkylation of 2-methyl-N-heteroaromatics with alcohols has been achieved via SN1-type C(sp3)-H functionalization, providing a green and efficient synthesis of indole and ferrocene-functionalized N-heteroaromatics in high yields.