Harnessing Latent Leaving Groups to Control the Divergent Synthesis of Unsymmetric and Symmetric Dienes
Year: 2026
Type: preprint
Abstract: Conjugated dienes are common feedstocks and motifs in biologically active molecules, dyes, and optoelectronics. However, the synthesis of unsymmetric variants often requires the stepwise functionalization of desymmetrized diene cores or the coupling of two disparately substituted alkenes. Herein we report an alternative approach that enables the synthesis of both unsymmetric and symmetric 1,4-diaryl,-1,3-dienes from a single, unified butadiene surrogate with high stereo-, regio- and chemoselectivity as well as broad tolerance for reactive functional groups. Critical to our approach is the introduction of a latent quaternary ammonium leaving group, which can be used to effectively gate the selectivity-determining elimination step behind judicious choice of reaction conditions.
Source: ChemRxiv
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Funder: National Science Foundation
OpenAlex ID: W7207857626