Keywords
amino acid amides
aminocarbene complexes
chiral
complexes
gold complexes
isocyanide complexes
Palladium complexes
platinum complexes
Abstract
The reaction between enantiopure amino acid amides and metal-coordinated isocyanides such as cis-[Cl2M(CNR)2] (M = Pd, Pt) and [ClAu(CNR)] affords chiral acyclic diaminocarbene complexes in 64 to 91% yields with full retention of configuration at stereogenic centers. Structural analysis of the representative PdII complexes revealed isostructural enantiomeric pairs with slightly distorted square-planar geometry, featuring labile Pd–Cl bonds trans to the ADC ligand.
Funders
Russian Science Foundation
25-13-20028
References
1.
Hopkinson M.N., Richter C., Schedler M., Glorius F.
Nature,
2014
2.
Kinzhalov M.A., Luzyanin K.V.
Russian Journal of Inorganic Chemistry,
2022
3.
Luzyanin K.V., Kinzhalov M.A.
2024
4.
Kinzhalov M.A., Grachova E.V., Luzyanin K.V.
Inorganic Chemistry Frontiers,
2022
5.
Kinzhalov M.A., Luzyanin K.V.
Coordination Chemistry Reviews,
2019
6.
Ott I.
Advances in Inorganic Chemistry,
2020
7.
A Patil S., P Hoagland A., A Patil S., Bugarin A.
Future Medicinal Chemistry,
2020
8.
Mikhailov V.N., Korvinson K., Sorokoumov V.N.
Russian Journal of General Chemistry,
2016
9.
Knorn M., Lutsker E., Reiser O.
Organometallics,
2015
10.
Snead D.R., Inagaki S., Abboud K.A., Hong S.
Organometallics,
2010
11.
Barbazanges M., Fensterbank L.
ChemCatChem,
2012
12.
Handa S., Slaughter L.M.
Angewandte Chemie - International Edition,
2012
13.
Khrakovsky D.A., Tao C., Johnson M.W., Thornbury R.T., Shevick S.L., Toste F.D.
Angewandte Chemie - International Edition,
2016
14.
Anisimova T.B., Guedes da Silva M.F., Kukushkin V.Y., Pombeiro A.J., Luzyanin K.V.
Dalton Transactions,
2014
15.
Anisimova T.B., Kinzhalov M.A., Guedes da Silva M.F., Novikov A.S., Kukushkin V.Y., Pombeiro A.J., Luzyanin K.V.
New Journal of Chemistry,
2017
16.
Kinzhalov M.A., Boyarskiy V.P., Luzyanin K.V., Dolgushin F.M., Kukushkin V.Y.
Dalton Transactions,
2013
17.
Luzyanin K.V., Tskhovrebov A.G., Carias M.C., Guedes da Silva M.F., Pombeiro A.J., Kukushkin V.Y.
Organometallics,
2009
18.
Kinzhalov M.A., Boyarskii V.P.
Russian Journal of General Chemistry,
2015
19.
Hashmi A.S., Lothschütz C., Böhling C., Rominger F.
Organometallics,
2011
20.
Melnik M.V., Mikhaylov V.N., Novikov A.S., Kinzhalov M.A., Bunev A.S., Kryukova M.A., Sorokoumov V.N., Balova I.A.
Organometallics,
2024
21.
Wanniarachchi Y.A., Slaughter L.M.
Organometallics,
2008
22.
Kinzhalov M.A., Kashina M.V., Mikherdov A.S., Mozheeva E.A., Novikov A.S., Smirnov A.S., Ivanov D.M., Kryukova M.A., Ivanov A.Y., Smirnov S.N., Kukushkin V.Y., Luzyanin K.V.
Angewandte Chemie - International Edition,
2018
23.
Arunan E., Desiraju G.R., Klein R.A., Sadlej J., Scheiner S., Alkorta I., Clary D.C., Crabtree R.H., Dannenberg J.J., Hobza P., Kjaergaard H.G., Legon A.C., Mennucci B., Nesbitt D.J.
Pure and Applied Chemistry,
2011
24.
Bondi A.
The Journal of Physical Chemistry,
1964
25.
Fuster F., Grabowski S.J.
Journal of Physical Chemistry A,
2011
26.
Savin A., Nesper R., Wengert S., Fässler T.F.
1997
27.
Silvi B., Savin A.
Nature,
1994
28.
Steiner T., Desiraju G.R.
Chemical Communications,
1998
29.
Baker E.N., Hubbard R.E.
Progress in Biophysics and Molecular Biology,
1984
30.