What is it about?

Chiral ferrocenyl derivatives are imporant as ligands for asymmetric catalysis. This paper show that Pd-complexes with N-protected aminoacids such as N-Boc-alanine are competent catalysts for diastereoselective arylation of chiral ferrocenylmethanamines. As arylation reagents in this protocol, arylboronic acids and pinacol eters can be employed.

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Why is it important?

Chiral metallocene compounds found use in pharmaceutical and chemical industry as catalysts for syntheses chiral medicines or crop protection agents. Efficient synthesis of useful chiral ferrocenyl derivatives can be accomplished also via C-H activation strategy using Pd-catalysis. This methodology is complementary to traditional methods, which utilize diastereoselective lithiations.


Work on this article was very special and exciting to me because, we have always used ortho-lithiations for making chiral ferrocenes and here for the first time, we have ventured into new territory of metal-catalyzed C-H activation.

Professor Radovan Sebesta
Comenius University in Bratislava

Read the Original

This page is a summary of: Diastereoselective Pd-Catalyzed C–H Arylation of Ferrocenylmethanamines with Arylboronic Acids or Pinacol Esters, The Journal of Organic Chemistry, May 2019, American Chemical Society (ACS), DOI: 10.1021/acs.joc.9b00953.
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