2014 年 72 巻 1 号 p. 39-50
The functional group manipulation is fundamental in synthetic organic chemistry. Hence, the development of chemoselective hydrogenation methods using a heterogeneous catalyst has been a topic of sustained interest in a synthetic organic chemistry. While many applications to achieve a chemoselective catalyst system have been evaluated, only a few studies such as Lindlar catalyst and Rosenmund’s reaction have been accepted as general chemoselective methodologies. We have successfully developed useful heterogeneous catalysts such as a combination of Pd/C and a nitrogen-containing base, Pd/C-ethylenediamine complex [Pd/C(en)], Pd/C-diphenyl sulfide complex [Pd/C(Ph2S)], Pd-fibroin complex [Pd/Fib], Pd-molecular sieves complex (Pd/MS), Pd-boron nitride complex (Pd/BN), Pd-polyethyleneimine complex (Pd/PEI), and a combination of Pd/BN and a nitrogen-containing base, possessing specific characteristics and suppressed catalyst activities to enable the reliable and chemoselective hydrogenation among various reducible functionalities. This review provides a brief overview of each of the catalyst systems with a focus on specific features and catalyst activities in a comprehensive manner.