Premium
Rhodium‐Catalyzed Bis‐ Hydroaminomethylation of Linear Aliphatic Alkenes with Piperazine
Author(s) -
Seidensticker Thomas,
Vosberg Jonas M.,
Ostrowski Karoline A.,
Vorholt Andreas J.
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500896
Subject(s) - chemistry , catalysis , alkene , piperazine , rhodium , yield (engineering) , tandem , organic chemistry , combinatorial chemistry , medicinal chemistry , thermodynamics , materials science , composite material , physics
An efficient protocol was developed to prepare a series of dialkylpiperazines via Rh‐catalyzed bis ‐hydroaminomethylation of linear aliphatic alkenes with piperazine. The well‐known Rh/Biphephos catalytic system was applied, yielding the desired dialkylpiperazines within six tandem catalytic steps, already at low catalyst loadings of 0.1 mol%. For the model alkene 1‐octene, good yields and linearities of 80% and 77:23, respectively, were achieved under optimized conditions. Influences on the catalytic system regarding n / iso ratio, possible side reactions and the reaction path are discussed on the basis of yield vs. time plots and parameter optimization. With the developed general protocol, other linear, functionalized and branched substrates were effectively transformed to the corresponding linear N,N ‐disubstituted piperazines.