Journal
ACS CATALYSIS
Volume 6, Issue 1, Pages 381-388Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b02160
Keywords
iron catalysis; borrowing hydrogen; homogeneous catalysis; benzylamines; alcohol to amine transformation
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Funding
- Ministry of Education, Culture and Science [024.001.035]
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Benzylamines play a prominent role in numerous pharmaceutically active compounds. Thus, the development of novel, sustainable catalytic methodologies to provide access to these privileged structural motifs is of central importance. Herein we describe a systematic study for the construction of a large variety of benzylamines using a well-defined homogeneous iron complex. The methodology consists of the direct coupling of readily available benzyl alcohols with simpler amines through the borrowing hydrogen methodology, producing a variety of substituted secondary and tertiary benzylamines in moderate to excellent yields for the first time with an iron catalyst. Notably, we explore the versatility of this methodology in the one-pot synthesis of nonsymmetric tertiary amines, sequential functionalization of diols with distinctly different amines, and the synthesis of N-benzyl piperidines via various synthetic pathways. In addition, direct conversion of the renewable building block 2,5-furan-dinaethanol to pharmaceutically relevant compounds is achieved.
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