Remarkable ligand effect in Ni- and Pd-catalyzed bisthiolation and bisselenation of terminal alkynes: solving the problem of stereoselective dialkyldichalcogenide addition to the C triple chemical bond C Bond

Chemistry : a European Journal
Valentine P AnanikovMikhail Yu Antipin

Abstract

We have developed two new catalytic systems based on Ni and Pd complexes to solve the challenging problem of dialkyldichalcogenide (Alk2E2; E=S, Se) addition to alkynes. A comparative study of two catalytic systems-Ni/PMe2Ph and Pd/PCy2Ph-has revealed that the Ni catalyst is superior with respect to high catalytic activity and more general scope relative to the Pd system. A novel synthetic methodology was developed for the preparation of (Z)-bis(alkylthio)alkenes and (Z)-bis(alkylseleno)alkenes from terminal alkynes with excellent stereoselectivity and high yields.

References

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Citations

Apr 30, 2017·Chemical Science·Sergey S ZalesskiyValentine P Ananikov
Jul 27, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Irina Beletskaya, Vladimir Tyurin
Oct 28, 2019·Chemistry : a European Journal·Bin LiuGarret M Miyake
Oct 23, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Rohit Singh ChauhanVimal K Jain
Mar 10, 2011·Journal of Computational Chemistry·Meiyan WangZhijian Wu
Nov 10, 2013·Chemistry, an Asian Journal·Masayuki IwasakiYasushi Nishihara
Feb 16, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Valentine P Ananikov, Irina P Beletskaya
Apr 2, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Damir A SafinF Ekkehardt Hahn
Nov 30, 2013·Chemistry : a European Journal·Leonid V Romashov, Valentine P Ananikov
Aug 19, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sumbal SabaAntonio L Braga
Mar 20, 2019·Journal of the American Chemical Society·Kangbao ZhongRuopeng Bai

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