Hybrid Catalysis Enabling Room-Temperature Hydrogen Gas Release from N-Heterocycles and Tetrahydronaphthalenes

• DOI: 10.1021/jacs.7b00253
• Publication Date: 2017-01-31T15:43:47Z
• Authors: Shota Kato; Yutaka Saga; Masahiro Kojima; Hiromu Fuse; Shigeki Matsunaga; Arisa Fukatsu; Mio Kondo; Shigeyuki Masaoka; Motomu Kanai
• Keywords: 01 natural sciences; 7. Clean energy; 0104 chemical sciences

Hybrid catalyst systems to achieve acceptorless dehydrogenation of N-heterocycles and tetrahydronaphthalenes-model substrates for liquid organic hydrogen carriers-were developed. A binary hybrid catalysis comprising an acridinium photoredox catalyst and a Pd metal catalyst was effective for the dehydrogenation of N-heterocycles, whereas a ternary hybrid catalysis comprising an acridinium photoredox catalyst, a Pd metal catalyst, and a thiophosphoric imide organocatalyst achieved dehydrogenation of tetrahydronaphthalenes. These hybrid catalyst systems allowed for 2 molar equiv of H2 gas release from six-membered N-heterocycles and tetrahydronaphthalenes under mild conditions, i.e., visible light irradiation at rt. The combined use of two or three different catalyst types was essential for the catalytic activity.