The Ryu Research Group, Department of Chemistry, Graduate School of Science, Osaka Prefecture University

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Published in 2020

Org. Chem. Front., 2020, 7, 1266-1270 cover-01
Pd/light-induced alkyl–alkenyl coupling reaction between unactivated alkyl iodides and alkenylboronic acids
Huang, Hsin-Ju , Wang, Yi-Ting, Wu, Yen-Ku, Ryu, Ilhyong
Org. Chem. Front., 2020, 7, 10 pp. 1266 - 1270


Alkyl–alkenyl coupling reaction between unactivated alkyl iodides and 2-arylalkenylboronic acids utilizing a Pd/light combined system was studied. This reaction provided 2-alkylarylalkenes in good yields. It is proposed that in this reaction alkyl radicals are formed by SET from a Pd catalyst to alkyl iodides, which then undergo addition reactions to form C–C double bonds of alkenyl boronic acids and the subsequent β-fragmentation of boronyl radicals leads to the formation of alkyl-substituted arylalkenes.

Synthesis of Aliphatic Amides through a Photoredox Catalyzed Radical Carbonylation Involving Organosilicates as Alkyl Radical Precursors
Cartier, Alex, Levernier, Etienne, Dhimane, Anne-Lise , Fukuyama, Takahide , Ollivier, Cyril, Ryu, Ilhyong, Fensterbankb, Louis
Adv. Synth. Catal., 2020, 362, 10 pp. 2254 - 2259
DOI: 10.1002/adsc.202000314


Alkyl radicals, from primary to tertiary, formed by photocatalyzed oxidation of organosilicates, are involved efficiently in radical carbonylation with carbon monoxide (CO), in the presence of various amines and CCl4, leading to a variety of amides in moderate to good yields.

Syntheses of Diarylethenes by Perylene-catalyzed Photodesulfonylation from Ethenyl Sulfones
Watanabe, Hikaru, Takemto, Mai, Adachi, Kazumasa, Okuda, Yasuhiro, Dakegata, Aki, Fukuyama, Takahide, Ryu, Ilhyong, Wakamatsu, Kan, Orita, Akihiro
Chem. Lett., 2020, 49, 4 pp. 409 - 412
DOI: 10.1246/cl.200046


Diarylethenes were obtained from the corresponding ethenyl sulfones by photocatalyzed desulfonylation using UV or blue LEDs. When perylene and i-Pr2NEt were used as a photocatalyst and a sacrificing reagent, respectively, this desulfonylation proceeded smoothly to afford the desired ethenes with the functional groups such as chloro, alkoxy and heteroaromatic rings remaining untouched. The use of a flow photoreactor enabled this desulfonylation to proceed more rapidly to finish in an hour of residence time.

Eur JOC 2019.2019.45 cover
Site-Selective C(sp3)–H Functionalization of Fluorinated Alkanes Driven by Polar Effects Using a Tungstate Photocatalyst
Fukuyama, Takahide, Nishikawa, Tomohiro, Ryu, Ilhyong
Eur. J. Org. Chem., 2020, 2020, 10 pp. 1424 - 1428
DOI: 10.1002/ejoc.201901135

2019.2019.45 abstract

The TBADT‐catalyzed C(sp3)–H functionalization of perfluorophenyl‐ and perfluoroalkyl‐substituted alkanes was studied to determine how the fluorous substituents affect site‐selectivity. Alkylation of alkyl‐substituted perfluorobenzene avoids α‐C–H bonds, unlike their alkylbenzene counterparts, allowing site‐selective functionalization of C–H bonds remote to the aromatic ring. Alkylation of alkanes having a perfluoroalkyl group also avoided α‐C–H bonds. Radical polar effects in the SH2 transition states could explain this avoidance of α‐C–H functionalization.



Laboratory for Advanced Organic Synthesis
Organization for Research Promotion Osaka Prefecture University
Sakai, Osaka 599-8531, JAPAN
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