Litcius/Paper detail

Late-Stage Modification of Tertiary Phosphines via Ruthenium(II)-Catalyzed C–H Alkylation

Jiawei Li, Liang‐Neng Wang, Ming Li, Pan‐Ting Tang, Ni‐Juan Zhang, Li Tian, Xiao-Peng Luo, Mohamedally Kurmoo, Yue‐Jin Liu, Ming‐Hua Zeng

2020Organic Letters40 citationsDOI

Abstract

Ru(II)-catalyzed direct alkylation of tertiary phosphines via hydroarylation of activated olefins promoted by mono-N-protected amino acid (MPAA) was achieved. This protocol provides a straightforward access to a large library of Buchwald-type bulky alkylated monophosphines from commercially available biaryl phosphine. Moreover, two ruthenacycle intermediates of tertiary phosphines via C–H bond cleavage were isolated to illustrate the mechanism of P(III)-directed C–H activation.

Topics & Concepts

ChemistryRutheniumAlkylationCatalysisMedicinal chemistryStage (stratigraphy)Combinatorial chemistryOrganic chemistryPaleontologyBiologyAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions