Light-controlled pKa value of chiral Bronsted acid catalysts in enantioselective aza-Friedel-Crafts reaction

被引：3

作者：

Krishnan, Chandu G. ^{[1
]}

Kondo, Masaru ^{[2
]}

Yasuda, Osamu ^{[1
]}

Fan, Duona ^{[1
]}

Nakamura, Kento ^{[1
]}

Wakabayashi, Yoshitomo ^{[1
]}

Sasai, Hiroaki ^{[1
,3
]}

Takizawa, Shinobu ^{[1
]}

机构：

[1] Osaka Univ, SANKEN, Ibaraki Shi, Ibaraki, Osaka 5670047, Japan

[2] Ibaraki Univ, Grad Sch Sci & Engn, Hitachi, Ibaraki 3168511, Japan

[3] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 66期

基金：

日本学术振兴会;

关键词：

PHOSPHORIC-ACIDS; PHOTOSWITCHABLE ORGANOCATALYSIS; PHOTOCHROMIC DIARYLETHENES; SYSTEM; PHOTOMODULATION; INHIBITION; ACTIVATION; MEMORIES; INDOLES;

D O I：

10.1039/d3cc02719h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bis(dithienylethene)-based BINOL-derived phosphoric acid (DTE-BPA) has been developed as a light-controlled chiral organocatalyst for the first time. The photoinduced modulation of the reactivity and selectivity via the open/close isomerization of the DTE scaffold led to superior light-controlled ability in the enantioselective aza-Friedel-Crafts reaction of aldimines with indoles. DFT studies showed that photoisomerization is accompanied by a shift of 1.1 pK(a) units between the open and closed isomers.

引用

页码：9956 / 9959

页数：5