Ruthenium-Catalyzed Heck-Type Regioselective Benzylation of Terminal Alkynes via the Cleavage of Carbon-Carbon Triple Bond
Weifeng Xu , Biquan Xiong , Longzhi Zhu , Shipan Xu , Zhengong Meng , Wai-Yeung Wong
Chinese Journal of Chemistry ›› 2026, Vol. 44 ›› Issue (9) : 1406 -1418.
An innovative and highly regioselective strategy has been developed for synthesizing Heck-type products of (E)- and (Z)-prop-1-ene-1,3-diyldiaryls by benzylation of alkynes through cleaving the carbon-carbon triple bond of terminal alkynes. This method involves using a functionalized heterogeneous ruthenium-chitosan based catalyst, which can be easily recycled by filtering and washing with solvent post-reaction. By adopting this approach, the need for highly toxic alkyl halides, oxidants, and activation reagents is eliminated, while ensuring excellent E/Z selectivity in the formation of desired Heck-type benzylation products in satisfactory yields. To further investigate the reaction mechanism, comprehensive step-by-step control experiments and DFT calculations were conducted, shedding light on potential implications for the synthesis of biologically active (Z)- and (E)-prop-1-ene-1,3-diyldiarenes.
Heterogeneous catalysis / C–C triple bond cleavage / Terminal alkynes / Heck-type regioselective benzylation / Alkenes / Ruthenium / DFT calculation / Reaction mechanisms
2026 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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