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Keywords:

  • alkylation;
  • catalysis;
  • Grignard reagents;
  • isotopic labeling;
  • titanium isopropoxide

Abstract

The reactivity of Grignard reagents towards imines in the presence of catalytic and stoichiometric amounts of titanium alkoxides is reported. Alkylation, reduction, and coupling of imines take place. Whereas reductive coupling is the major reaction in stoichiometric reactions, alkylation is favored in catalytic reactions. Mechanistic studies clearly indicate that intermediates involved in the two reactions are different. Catalytic reactions involve a metal–alkyl complex. This has been confirmed by reactions of deuterium-labeled substrates and different alkylating agents. Under the stoichiometric conditions, however, titanium olefin complexes are formed through reductive elimination, probably through a multinuclear intermediate.

Featured Compounds

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  1. 1 - 18
Compound 1a
Molecular Weight:181.2331
Molecular Formula:C13H11N
InChIKey:UVEWQKMPXAHFST-KAMYIIQDSA-N
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Compound 2a
Molecular Weight:211.3022
Molecular Formula:C15H17N
InChIKey:KYJKITQCBFVYDT-UHFFFAOYSA-N
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Compound 5
Molecular Weight:284.215
Molecular Formula:C12H28O4Ti
InChIKey:VXUYXOFXAQZZMF-UHFFFAOYSA-N
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Compound 4
Molecular Weight:183.249
Molecular Formula:C13H13N
InChIKey:Not Available
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Compound 3
Molecular Weight:364.4822
Molecular Formula:C26H24N2
InChIKey:CHPLWMDKGMHCNY-UHFFFAOYSA-N
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Compound 7
Molecular Weight:435.422
Molecular Formula:C24H37NO3Ti
InChIKey:HSUFKLOYNCEWHA-UHFFFAOYSA-N
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Compound 6a
Molecular Weight:254.189
Molecular Formula:C11H26O3Ti
InChIKey:XXTPCABYRDQKAJ-UHFFFAOYSA-N
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Compound 9a
Molecular Weight:347.274
Molecular Formula:C19H25NO2Ti
InChIKey:HKWMRWUOJDQPQT-UHFFFAOYSA-N
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Compound 9b
Molecular Weight:528.507
Molecular Formula:C32H36N2O2Ti
InChIKey:OVKZKGMVGOQOKO-UHFFFAOYSA-N
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Compound 10
Molecular Weight:375.327
Molecular Formula:C21H29NO2Ti
InChIKey:WTQBJIGVPJHOPI-UHFFFAOYSA-N
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Compound 12
Molecular Weight:225.3288
Molecular Formula:C16H19N
InChIKey:WJPUHWWOXVFGQJ-UHFFFAOYSA-N
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Compound 13
Molecular Weight:225.3288
Molecular Formula:C16H19N
InChIKey:HKLQDCYJTPJFCM-UHFFFAOYSA-N
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Compound 2a1
Molecular Weight:214.3207
Molecular Formula:C15H17N
InChIKey:Not Available
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Compound 2a3
Molecular Weight:213.3145
Molecular Formula:C15H17N
InChIKey:Not Available
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Compound 2a2
Molecular Weight:213.3145
Molecular Formula:C15H17N
InChIKey:Not Available
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Compound 6e
Molecular Weight:257.208
Molecular Formula:C11H26O3Ti
InChIKey:Not Available
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Compound 6f
Molecular Weight:256.202
Molecular Formula:C11H26O3Ti
InChIKey:Not Available
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Compound 3
Molecular Weight:364.4822
Molecular Formula:C26H24N2
InChIKey:CHPLWMDKGMHCNY-UHFFFAOYSA-N
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  1. 1 - 18