Brønsted Acid-Promoted C–H Bond Cleavage via Electron Transfer from Toluene Derivatives to a Protonated Nonheme Iron(IV)-Oxo Complex with No Kinetic Isotope Effect

2013 ◽  
Vol 135 (13) ◽  
pp. 5052-5061 ◽  
Author(s):  
Jiyun Park ◽  
Yong-Min Lee ◽  
Wonwoo Nam ◽  
Shunichi Fukuzumi
Keyword(s):  
Electron Transfer ◽  
Isotope Effect ◽  
Kinetic Isotope Effect ◽  
Bond Cleavage ◽  
Nonheme Iron ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Kinetic Isotope ◽  
Brönsted Acid

Synthesis of 1-Alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones through Gold/Brønsted Acid Relay Actions: Observation of Selective C=C Bond Cleavage of Enaminones

Synthesis ◽  
2017 ◽  
Vol 49 (16) ◽  
pp. 3609-3618 ◽  
Author(s):  
Yanzhong Li ◽  
Yulei Zhao ◽  
Yang Yuan ◽  
Lingkai Kong ◽  
Fangfang Zhang
Keyword(s):  
Reaction Mechanism ◽  
Bond Cleavage ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Reaction Conditions ◽  
One Pot ◽  
Esi Ms ◽  
Ms Analysis ◽  
Brönsted Acid

A novel gold(I)/Brønsted acid sequential catalyzed/promoted procedure to synthesize 1-alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones under mild reaction conditions is developed. This methodology is realized by relay actions of gold and a Brønsted acid in a one-pot multistep manner. The gold(I)-catalyzed chemoselective C(sp2)-H functionalization of enaminones and Brønsted acid promoted cleavage of the C=C bond are integrated effectively. Based on the results of control experiments and ESI-MS analysis, a possible reaction mechanism is proposed.

Domino construction of a bullataketal core via double bond cleavage in activated dihydrofurans

2018 ◽  
Vol 5 (10) ◽  
pp. 1655-1663 ◽  
Author(s):  
Konstantin L. Ivanov ◽  
Ivan M. Vatsouro ◽  
Stanislav I. Bezzubov ◽  
Mikhail Ya. Melnikov ◽  
Ekaterina M. Budynina
Keyword(s):  
Double Bond ◽  
Bond Cleavage ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Biologically Relevant ◽  
Brönsted Acid

A new rapid approach to structurally challenging and biologically relevant methanobenzodioxepines was developed via a Brønsted acid-triggered domino transformation of 3-carbonyl-4,5-dihydrofurans, substituted with MOM-protected o-hydroxyaryls at the C4 atom.

Brønsted acid-catalyzed selective C–C bond cleavage of 1,3-diketones: a facile synthesis of 4(3H)-quinazolinones in aqueous ethyl lactate

RSC Advances ◽  
2015 ◽  
Vol 5 (104) ◽  
pp. 85646-85651 ◽  
Author(s):  
Guanshuo Shen ◽  
Haifeng Zhou ◽  
Peng Du ◽  
Sensheng Liu ◽  
Kun Zou ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Ethyl Lactate ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Facile Synthesis ◽  
Brönsted Acid ◽  
Acid Catalyzed

A Two-State Reactivity Model Explains Unusual Kinetic Isotope Effect Patterns in CH Bond Cleavage by Nonheme Oxoiron(IV) Complexes

2009 ◽  
Vol 121 (7) ◽  
pp. 1317-1321 ◽  
Author(s):  
Eric J. Klinker ◽  
Sason Shaik ◽  
Hajime Hirao ◽  
Lawrence Que
Keyword(s):  
Isotope Effect ◽  
Kinetic Isotope Effect ◽  
Bond Cleavage ◽  
Kinetic Isotope

scholarly journals Kinetic isotope effect of proton-coupled electron transfer in a hydrogen bonded phenol–pyrrolidino[60]fullerene

2015 ◽  
Vol 14 (12) ◽  
pp. 2147-2150 ◽  
Author(s):  
Janneke Ravensbergen ◽  
Chelsea L. Brown ◽  
Gary F. Moore ◽  
Raoul N. Frese ◽  
Rienk van Grondelle ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Isotope Effect ◽  
Kinetic Isotope Effect ◽  
Proton Coupled Electron Transfer ◽  
Kinetic Isotope ◽  
Hydrogen Bonded

Proton-coupled electron transfer (PCET) plays a central role in photosynthesis and potentially in solar-to-fuel systems.

Sign in / Sign up

Export Citation Format

Share Document