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A highly reactive titanium precatalyst for intramolecular hydroamination reactions
Lutz Ackermann1, Robert G Bergman
1Department of Chemistry and Center for New Directions in Organic Synthesis, University of California, Berkeley, California 94720-1460, USA.
Organic Letters
|April 27, 2002
Summary
Tetrakisamido titanium complexes show enhanced activity in intramolecular hydroamination reactions compared to Cp2TiMe2. The bis(sulfonamido) complex 11 offers superior selectivity and reactivity for aminoallene hydroamination.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Synthetic Organic Chemistry
Background:
- Titanium complexes are widely studied catalysts.
- Intramolecular hydroamination is a key synthetic transformation.
- Cp2TiMe2 is a known titanium catalyst.
Purpose of the Study:
- To compare the activity of tetrakisamido titanium complexes with Cp2TiMe2.
- To investigate the regioselectivity of intramolecular hydroamination of aminoallenes.
- To identify optimal precatalysts for these transformations.
Main Methods:
- Synthesis and characterization of tetrakisamido titanium complexes.
- Testing catalytic activity in intramolecular hydroamination of aminoalkynes and aminoallenes.
- Analysis of reaction regioselectivity based on precatalyst structure.
Main Results:
- Tetrakisamido titanium complexes exhibit significantly higher activity than Cp2TiMe2.
- The regioselectivity of aminoallene hydroamination is dependent on the precatalyst.
- Bis(sulfonamido) complex 11 provides the most selective and reactive catalysis.
Conclusions:
- Tetrakisamido titanium complexes represent a promising class of catalysts for hydroamination.
- Precise catalyst design, specifically the bis(sulfonamido) ligand, is crucial for controlling regioselectivity.
- Complex 11 is a highly effective precatalyst for the intramolecular hydroamination of aminoallenes.