Synthesis 2022; 54(21): 4721-4726
DOI: 10.1055/a-1668-2075
special topic
Asymmetric C–H Functionalization

Synthesis of Ruthenium Catalysts with a Chiral Arene Ligand Derived from Natural Camphor

Roman A. Pototskiy
a   A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova Street, Moscow 119991, Russian Federation
,
Mikhail A. Boym
a   A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova Street, Moscow 119991, Russian Federation
b   National Research University Higher School of Economics, 20 Miasnitskaya Street, Moscow 101000, Russian Federation
,
Yulia V. Nelyubina
a   A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova Street, Moscow 119991, Russian Federation
,
a   A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova Street, Moscow 119991, Russian Federation
b   National Research University Higher School of Economics, 20 Miasnitskaya Street, Moscow 101000, Russian Federation
› Author Affiliations
This work was supported by the Russian Science Foundation (grant # 17-73-20144). X-ray diffraction data were collected using the equipment of the Center for molecular composition studies of INEOS RAS with financial support from the Ministry of Science and Higher Education of the Russian Federation.


Abstract

A ruthenium complex with a chiral arene ligand [(camphor–arene)RuCl2]2 was synthesized by the reaction of RuCl3·nH2O with a chiral diene which was obtained from natural camphor in three steps. This complex catalyzed the asymmetric hydrogenation of acetophenone (64–85% ee), but decomposed in catalytic reactions involving C–H activation of 2-phenylpyridine or benzoic acid derivatives.

Supporting Information



Publication History

Received: 28 September 2021

Accepted after revision: 13 October 2021

Accepted Manuscript online:
13 October 2021

Article published online:
22 November 2021

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