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Updated: Feb 9, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Radical-Polar Crossover Reactions of Dienylboronate Complexes: Synthesis of Functionalized Allylboronic Esters
Marvin Kischkewitz1, Carolin Gerleve1, Armido Studer1
1Institute of Organic Chemistry, Westfälische Wilhelms-Universität , Corrensstraße 40 , 48149 Münster , Germany.
Abstract:
Radical-polar crossover reactions of dienylboronate complexes are applied to the synthesis of functionalized secondary and tertiary allylboronic esters. The transition-metal-free three-component coupling uses readily accessible dienylboronate esters as substrates in combination with various sp3/sp2 carbon nucleophiles and commercial alkyl iodides as radical precursors. In the visible light-initiated radical chain process, two new C-C bonds are formed, and the E-double bond geometry in the product allylboronic esters is controlled with good to excellent selectivity.
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