Zirconoarylation of alkynes through p-chloranil-promoted reductive elimination of arylzirconates

• Xiaoyu Yan,
• Chao Chen and
• Chanjuan Xi

Beilstein J. Org. Chem. 2014, 10, 528–534, doi:10.3762/bjoc.10.48

• /bjoc.10.48 Abstract A novel method for the zirconoarylation of alkynes was developed. TCQ-promoted reductive elimination of arylzirconate [LiCp2ZrAr(RC≡CR)], which was prepared by the reaction of zirconocene–alkyne complexes with aryllithium compounds, afforded trisubstituted alkenylzirconocenes. This

• reaction can afford multi-substituted olefins with high stereoselectivity. Keywords: alkyne; multicomponent; reductive elimination; zirconate; zirconoarylation; Introduction The controlled synthesis of multi-substituted olefins is one of the most challenging tasks in organic synthesis [1][2]. A series of

• elimination to afford vinylzirconocene(II) 6. Then intermediate 6 reacts with TCQ to form vinylzirconocene(IV) 4. The intermediate 4 reacts with electrophiles to afford multi-substituted olefin 3. Conclusion We have developed a novel method for the zirconoarylation of alkynes through TCQ-promoted reductive