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
收藏
页码：9956 / 9959
页数：5
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