Reductive C(sp3)-C(sp3) homo-coupling of benzyl or allyl halides with H2 using a water-soluble electron storage catalyst

Takeshi Yatabe; Sayaka Futakuchi; Keishi Miyazawa; Daiki Shimauchi; Yukina Takahashi; Ki-Seok Yoon; Hidetaka Nakai; Seiji Ogo

doi:10.1039/d1ra08596d

Reductive C(sp³)-C(sp³) homo-coupling of benzyl or allyl halides with H₂ using a water-soluble electron storage catalyst

RSC Adv. 2021 Dec 9;11(62):39450-39454. doi: 10.1039/d1ra08596d. eCollection 2021 Dec 6.

Authors

Takeshi Yatabe^{1

2

3}, Sayaka Futakuchi¹, Keishi Miyazawa¹, Daiki Shimauchi¹, Yukina Takahashi^{1

2}, Ki-Seok Yoon^{1

2

3}, Hidetaka Nakai⁴, Seiji Ogo^{1

2

3}

Affiliations

¹ Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University 744 Moto-oka, Nishi-ku Fukuoka 819-0395 Japan ogo.seiji.872@m.kyushu-u.ac.jp.
² International Institute for Carbon-Neutral Energy Research (WPI-I2CNER), Kyushu University 744 Moto-oka, Nishi-ku Fukuoka 819-0395 Japan.
³ Center for Small Molecule Energy, Kyushu University 744 Moto-oka, Nishi-ku Fukuoka 819-0395 Japan.
⁴ Department of Applied Chemistry, Faculty of Science and Engineering, Kindai University 3-4-1 Kowakae, Higashi-Osaka Osaka 577-8502 Japan.

Abstract

This paper reports the first example of a reductive C(sp³)-C(sp³) homo-coupling of benzyl/allyl halides in aqueous solution by using H₂ as an electron source {turnover numbers (TONs) = 0.5-2.3 for 12 h}. This homo-coupling reaction, promoted by visible light, is catalysed by a water-soluble electron storage catalyst (ESC). The reaction mechanism, and four requirements to make it possible, are also described.