Transition‐Metal‐Free Synthesis of Polyfunctional Triarylmethanes and 1,1‐Diarylalkanes by Sequential Cross‐Coupling of Benzal Diacetates with Organozinc Reagents

Abstract

Abstract A variety of functionalized triarylmethane and 1,1‐diarylalkane derivatives were prepared via a transition‐metal‐free, one‐pot and two‐step procedure, involving the reaction of various benzal diacetates with organozinc reagents. A sequential cross‐coupling is enabled by changing the solvent from THF to toluene, and a two‐step S N 1‐type mechanism was proposed and evidenced by experimental studies. The synthetic utility of the method is further demonstrated by the synthesis of several biologically relevant molecules, such as an anti‐tuberculosis agent, an anti‐breast cancer agent, a precursor of a sphingosine‐1‐phosphate (S1P) receptor modulator, and a FLAP inhibitor.