Open AccessGeneral and Efficient C–C Bond Forming Photoredox Catalysis with Semiconductor Quantum Dots
Author(s) -
Jill A. Caputo,
Leah C. Frenette,
Norman Zhao,
Kelly L. Sowers,
Todd D. Krauss,
Daniel J. Weix
Publication year - 2017
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.6b13379
Subject(s) - photoredox catalysis , chemistry , catalysis , quantum dot , amine gas treating , redox , alkylation , nanocrystal , photochemistry , halogenation , photocatalysis , metal , combinatorial chemistry , molecule , nanotechnology , organic chemistry , materials science
Photoredox catalysis has become an essential tool in organic synthesis because it enables new routes to important molecules. However, the best available molecular catalysts suffer from high catalyst loadings and rely on precious metals. Here we show that colloidal nanocrystal quantum dots (QDs) can serve as efficient and robust, precious-metal free, photoassisted redox catalysts. A single-sized CdSe quantum dot (3.0 ± 0.2 nm) can replace several different dye catalysts needed for five different photoredox reactions (β-alkylation, β-aminoalkylation, dehalogenation, amine arylation, and decarboxylative radical formation). Even without optimization of the QDs or the reaction conditions, efficiencies rivaling those of the best available metal dyes were obtained.