Harnessing Latent Leaving Groups to Control the Divergent Synthesis of Unsymmetric and Symmetric Dienes
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.
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BibTeX
@misc{reddy2026harnessing,
title = {{Harnessing Latent Leaving Groups to Control the Divergent Synthesis of Unsymmetric and Symmetric Dienes}},
author = {Mandapati Bhargava Reddy and Prerana Masurkar and Raj Debnath and Quinton J. Bruch},
howpublished = {ChemRxiv},
year = {2026},
month = sep,
doi = {10.26434/chemrxiv.15008228/v1},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008228/v1},
note = {CC BY-NC-ND},
}
RIS
TY - UNPB
TI - Harnessing Latent Leaving Groups to Control the Divergent Synthesis of Unsymmetric and Symmetric Dienes
AU - Mandapati Bhargava Reddy
AU - Prerana Masurkar
AU - Raj Debnath
AU - Quinton J. Bruch
PY - 2026
DA - 2026/09/02
PB - ChemRxiv
DO - 10.26434/chemrxiv.15008228/v1
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008228/v1
AB - 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.
ER -