Donor-Acceptor π-Conjugated Enamines: Functional Group-Compatible Synthesis from Amides and Their Photoabsorption and Photoluminescence Properties

Autor: Yoichiro Kuninobu, Ikumi Kitahara, Atsushi Tahara, Hideo Nagashima, Daichi Sakata
Rok vydání: 2019
Předmět:
Zdroj: The Journal of organic chemistry. 84(23)
ISSN: 1520-6904
Popis: High functional group compatibility of iridium-catalyzed synthesis of enamines from amides and 1,1,3,3-tetramethyldisiloxane (TMDS) realized facile access of a series of donor (D)-π-acceptor (A)-conjugated enamines, in which enamine behaves as a donor functional group. The amide precursors containing reducible functional groups, such as halogen, carbonyl, and nitro groups, underwent reaction with TMDS to give the corresponding enamines in high yields. In most cases, chemoselective hydrosilane reduction of the amide group occurred while other reducible groups remained intact. Absorption and emission properties including solvatochromic behavior for the resulting D-π-A-conjugated enamines were determined using UV-visible and fluorescent spectra, which provided an understanding of the donor properties of the CH═CHNPh
Databáze: OpenAIRE