B(C6F5)3-Catalyzed Highly Chemoselective Reduction of Isatins: Synthesis of Indolin-3-ones and Indolines

Hyojin Jeong; Nara Han; Dong Wook Hwang; Haye Min Ko

doi:10.1021/acs.orglett.0c03150

B(C₆F₅)₃-Catalyzed Highly Chemoselective Reduction of Isatins: Synthesis of Indolin-3-ones and Indolines

Org Lett. 2020 Oct 16;22(20):8150-8155. doi: 10.1021/acs.orglett.0c03150. Epub 2020 Oct 6.

Authors

Hyojin Jeong¹, Nara Han¹, Dong Wook Hwang¹, Haye Min Ko^{1

2}

Affiliations

¹ Department of Chemistry, Wonkwang University, 460 Iksandae-ro, Iksan, Jeonbuk 54538, Republic of Korea.
² Wonkwang Institute of Materials Science and Technology, Wonkwang University, 460 Iksandae-ro, Iksan, Jeonbuk 54538, Republic of Korea.

PMID: 33021380
DOI: 10.1021/acs.orglett.0c03150

Abstract

A chemo- and site-selective reduction reaction of isatin derivatives using catalyst B(C₆F₅)₃ and hydrosilanes is described. This transformation is operationally simple, proceeds under mild conditions, and is resistant to various functional groups. Thus, this efficient reaction using a combination of B(C₆F₅)₃ and BnMe₂SiH or B(C₆F₅)₃ and Et₂SiH₂ could potentially be utilized to produce various indolin-3-ones and indolines, without the need for multistep procedures and metal catalysis conditions.