Self-Assembled Multilayer Iron(0) Nanoparticle Catalyst for Ligand-Free Carbon-Carbon/Carbon-Nitrogen Bond-Forming Reactions

Toshiki Akiyama; Yuki Wada; Makito Yamada; Yasunori Shio; Tetsuo Honma; Shuhei Shimoda; Kazuki Tsuruta; Yusuke Tamenori; Hitoshi Haneoka; Takeyuki Suzuki; Kazuo Harada; Hayato Tsurugi; Kazushi Mashima; Jun-Ya Hasegawa; Yoshihiro Sato; Mitsuhiro Arisawa

doi:10.1021/acs.orglett.0c02574

Self-Assembled Multilayer Iron(0) Nanoparticle Catalyst for Ligand-Free Carbon-Carbon/Carbon-Nitrogen Bond-Forming Reactions

Org Lett. 2020 Sep 18;22(18):7244-7249. doi: 10.1021/acs.orglett.0c02574. Epub 2020 Sep 9.

Authors

Affiliations

¹ Graduate School of Pharmaceutical Sciences, Osaka University, Yamada-oka 1-6, Suita, Osaka 565-0871, Japan.
² Japan Synchrotron Radiation Research Institute, 1-1-1 Kouto, Sayo-cho, Sayo-gun, Hyogo 679-5198, Japan.
³ Institute for Catalysis, Hokkaido University, Kita-21, Nishi-10, Kita-ku, Sapporo 001-0021, Japan.
⁴ The Institute of Scientific and Industrial Research, Osaka University, Mihoga-oka, Ibaraki, Osaka 567-0047, Japan.
⁵ Graduate School of Engineering Science, Osaka University, Machikaneyama 1-3, Toyonaka, Osaka 560-8531, Japan.
⁶ Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.

PMID: 32903001
DOI: 10.1021/acs.orglett.0c02574

Abstract

Self-assembled multilayer iron(0) nanoparticles (NPs, 6-10 nm), namely, sulfur-modified Au-supported Fe(0) [SAFe(0)], were developed for ligand-free one-pot carbon-carbon/carbon-nitrogen bond-forming reactions. SAFe(0) was successfully prepared using a well-established metal-nanoparticle catalyst preparative protocol by simultaneous in situ metal NP and nanospace organization (PSSO) with 1,4-bis(trimethylsilyl)-1,4-dihydropyrazine (Si-DHP) as a strong reducing agent. SAFe(0) was easy to handle in air and could be recycled with a low iron-leaching rate in reaction cycles.