In search of new organometallic reagents for organic synthesis

2005 ◽  
pp. 109-147 ◽  
Author(s):  
Thomas Kauffmann
Keyword(s):  
Organic Synthesis ◽  
Organometallic Reagents

A Different Approach to Enantioselective Organic Synthesis: Absolute Asymmetric Synthesis of Organometallic Reagents

2009 ◽  
Vol 121 (17) ◽  
pp. 3183-3186 ◽  
Author(s):  
Anders Lennartson ◽  
Susanne Olsson ◽  
Jonas Sundberg ◽  
Mikael Håkansson
Keyword(s):  
Asymmetric Synthesis ◽  
Organic Synthesis ◽  
Organometallic Reagents ◽  
Absolute Asymmetric Synthesis

Organometallic reagents in organic synthesis—VI

Tetrahedron ◽  
1979 ◽  
Vol 35 (9) ◽  
pp. 1183-1189 ◽  
Author(s):  
Robin A.J. Smith ◽  
Donald J. Hannah
Keyword(s):  
Organic Synthesis ◽  
Organometallic Reagents

scholarly journals Photocatalytic α-Alkylation of Amines with Alkyl Halides

2020 ◽  
Author(s):  
Lingying Leng ◽  
Joseph Ready
Keyword(s):  
Organic Synthesis ◽  
Nucleophilic Addition ◽  
Building Blocks ◽  
Alkyl Halides ◽  
Organometallic Reagents ◽  
Dehydrogenative Coupling ◽  
Alkyl Bromides ◽  
Alternative Approach ◽  
Traditionally Prepared ◽  
Carbon Centered Radical

a-Branched amines represent essential building blocks for organic synthesis. They are traditionally prepared through nucleophilic addition to imines. These methods often require highly reactive organometallic reagents and proceed under rigorous air- and moisture-free conditions. Here we describe an alternative approach that involves a net dehydrogenative coupling between alkyl bromides and amines. Mechanistically, the reaction likely involves photocatalytic generation of an a-amino radical and a stabilized carbon-centered radical (allyl, benzyl, a-carbonyl) followed by radical recombination. This approach offers a mild, atom-economical, redox neutral synthesis of a-branched amines that shows broad scope and avoids pre-metalated reagents.

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