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
相关论文
共 41 条
  • [31] Enantioselective Michael-type Friedel-Crafts reactions of indoles to enones catalyzed by a chiral camphor-based Bronsted acid
    Zhou, Wei
    Xu, Li-Wen
    Li, Lyi
    Yang, Lei
    Xia, Chun-Gu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (23) : 5225 - 5227
  • [32] Enantioselective Friedel-Crafts Alkylation Reaction of Heteroarenes with N-Unprotected Trifluoromethyl Ketimines by Means of Chiral Phosphoric Acid
    Miyagawa, Masamichi
    Yoshida, Masaru
    Kiyota, Yuki
    Akiyama, Takahiko
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (22) : 5677 - 5681
  • [33] Enantioselective Synthesis of Diarylmethylamines through the Aza-Friedel-Crafts Reaction of 1,3,5-Trialkoxy Benzenes and N-Sulfonyl Aldimines Catalyzed by BINOL-Derived Disulfonimides
    Jia, Zi-Hao
    Chen, Ling-Yan
    Zheng, Hao
    Li, Zhang-Rui
    Song, Qing-Chun
    Li, Ya
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (14) : 9720 - 9729
  • [34] Chiral Bronsted Acid-Catalyzed Intramolecular Asymmetric Dearomatization Reaction of Indoles with Cyclobutanones via Cascade Friedel-Crafts/Semipinacol Rearrangement
    Yu, Xuan
    Zheng, Chao
    You, Shu-Li
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (37) : 25878 - 25887
  • [35] DFT Study of Chiral-Phosphoric-Acid-Catalyzed Enantioselective Friedel-Crafts Reaction of Indole with Nitroalkene: Bifunctionality and Substituent Effect of Phosphoric Acid
    Hirata, Takashi
    Yamanaka, Masahiro
    CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (02) : 510 - 516
  • [36] Enantioselective activation of aldehydes by chiral phosphoric acid catalysts in an aza-ene-type reaction between glyoxylate and enecarbamate
    Terada, Masahiro
    Soga, Kazuyo
    Momiyama, Norie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) : 4122 - 4125
  • [37] Chiral Phosphoric Acid Catalyzed Enantioselective Friedel-Crafts Reaction of N-Protected 4-Aminoindoles with β,γ-Unsaturated α-Ketimino Esters
    Ding, Yu-Yang
    Xu, Deng-Feng
    Meng, Shan-Shui
    Li, Yang
    Zhao, Jun-Ling
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 664 - 669
  • [38] Protonated Bis-1,2,3-triazole as an Anion-Binding Chiral Bronsted Acid for Catalytic Asymmetric Friedel-Crafts Reaction of Indoles with Imines
    Furukawa, Yukino
    Suzuki, Ryuhei
    Nakashima, Tsubasa
    Gramage-Doria, Rafael
    Ohmatsu, Kohsuke
    Ooi, Takashi
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2018, 91 (08) : 1252 - 1257
  • [39] An organocatalytic asymmetric Friedel-Crafts reaction of 2-substituted indoles with aldehydes: enantioselective synthesis of α-hydroxyl ketones by low loading of chiral phosphoric acid
    Deng, Xiong-fei
    Wang, Ying-wei
    Zhang, Shi-qi
    Li, Ling
    Li, Guang-xun
    Zhao, Gang
    Tang, Zhuo
    CHEMICAL COMMUNICATIONS, 2020, 56 (16) : 2499 - 2502
  • [40] Chiral Bronsted acid-catalyzed Friedel-Crafts alkylation of electron-rich arenes with in situ-generated ortho-quinone methides: highly enantioselective synthesis of diarylindolylmethanes and triarylmethanes
    Saha, Satyajit
    Alamsetti, Santosh Kumar
    Schneider, Christoph
    CHEMICAL COMMUNICATIONS, 2015, 51 (08) : 1461 - 1464
12345