Early transition metal-catalyzed C–H alkylation: hydroaminoalkylation for Csp3–Csp3 bond formation in the synthesis of selectively substituted amines

2018 ◽  
Vol 54 (89) ◽  
pp. 12543-12560 ◽  
Author(s):  
P. M. Edwards ◽  
L. L. Schafer
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Protecting Group ◽  
Early Transition Metal ◽  
Directing Group ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Early Transition

Protecting group, directing group, and external oxidant free synthesis of structurally diverse amines.

Hydroaminoalkylation of Allenes

Synlett ◽  
2019 ◽  
Vol 30 (08) ◽  
pp. 967-971 ◽  
Author(s):  
Jens Bielefeld ◽  
Steffen Mannhaupt ◽  
Marc Schmidtmann ◽  
Sven Doye
Keyword(s):  
Transition Metal ◽  
Simple Explanation ◽  
Reaction Conditions ◽  
Titanium Catalyst ◽  
Early Transition Metal ◽  
Allylic Cation ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Early Transition

The first examples of early-transition-metal-catalyzed hydroaminoalkylation reactions of allenes are reported. Initial studies performed with secondary aminoallenes led to the identification of a suitable titanium catalyst and revealed that under the reaction conditions, the initially formed hydroaminoalkylation products undergo an unexpected titanium-catalyzed rearrangement to form the thermodynamically more stable allylamines. The assumption that this rearrangement involves a reactive allylic cation intermediate provides a simple explanation of the fact that no successful early-transition-metal-catalyzed hydroaminoalkylations of allenes have previously been reported. As a result of the generation of the corresponding cation, the titanium-catalyzed intermolecular hydroaminoalkylation of propa-1,2-diene unexpectedly gives an aminocyclopentane product formed by incorporation of two equivalents of propa-1,2-diene.

ChemInform Abstract: Early Transition Metal Catalyzed Hydrosilation Reaction

ChemInform ◽  
2010 ◽  
Vol 41 (23) ◽  
pp. no-no
Author(s):  
Fengyu Bao ◽  
Ken-ichiro Kanno ◽  
Tamotsu Takahashi
Keyword(s):  
Transition Metal ◽  
Early Transition Metal ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Early Transition

Hydroaminoalkylation: Early-Transition-Metal-Catalyzed α-Alkylation of Amines

Synthesis ◽  
2014 ◽  
Vol 46 (21) ◽  
pp. 2884-2896 ◽  
Author(s):  
Laurel Schafer ◽  
Eugene Chong ◽  
Pierre Garcia
Keyword(s):  
Transition Metal ◽  
Early Transition Metal ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Early Transition
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