Abstract
This chapter describes late transition metal complexes-catalyzed hydroamination, the formal addition of an H–N bond across a C–C multiple bond. Late transition metal catalysis has been intensely developed in the hydroamination and additions of various kinds of amines to C–C multiple bonds have been achieved. The reaction pathways strongly depend on the choice of metal complexes, substrates, and reaction conditions. This chapter is organized primarily based on the difference in the mechanisms of hydroamination reactions, and in the scope section concise summary of the hydroamination reaction is shown.
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Notes
- 1.
References attached with “*” are enantio-/diastereo-selective, or chirality transfer reactions.
Abbreviations
- Ar:
-
Aryl
- Bu:
-
Butyl
- cod:
-
1,5-Cyclooctadiene
- Cy:
-
Cyclohexyl
- d/D:
-
Deuterium
- dba:
-
Dibenzylideneacetone
- DPPPent:
-
1,5-Bis(diphenylphosphino)pentane
- Et:
-
Ethyl
- L:
-
Ligand
- M:
-
Metal or molar (mol dm−3)
- Me:
-
Methyl
- Nu:
-
Nucleophile
- P:
-
Phosphorus atom in ligand
- Pent:
-
Pentyl
- Ph:
-
Phenyl
- R:
-
Organic substituent or alkyl
- Tf:
-
Trifluoromethanesulfonyl
- Tol:
-
Tolyl
- Tol-BINAP:
-
2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl
- Triphos:
-
Bis(2-diphenylphosphinoethyl)phenylphosphine
- Ts:
-
p-Toluenesulfonyl (tosyl)
- X:
-
Halide
- Xantphos:
-
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
- Y:
-
Counter anion
References
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Nishina, N., Yamamoto, Y. (2012). Late Transition Metal-Catalyzed Hydroamination. In: Ananikov, V., Tanaka, M. (eds) Hydrofunctionalization. Topics in Organometallic Chemistry, vol 43. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_2012_31
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