Synthesis of β-fluorocarboxylic esters via organophotoredox-catalyzed fluoroalkoxycarbonylation of alkenes in EtOH

Abstract

An efficient and environmentally friendly organophotoredox-catalyzed method for the synthesis of β-fluorocarboxylic esters with a broad substrate scope in EtOH is developed. With this approach, a variety of potential biologically...

Intramolecular dehydrogenative amination of alkenes via dual organic photoredox and cobalt catalysis without a hydrogen acceptor

“…Based on the above experimental results as well as other reports, 15 a plausible pathway for this acceptorless dehydrogenative amination process is proposed and illustrated in Scheme 2. Irradiation of the ground-state photocatalyst Mes-AcrPh + BF 4 − with visible light produces the excited state [Mes-AcrPh + BF 4 − ]* ( E 1/2 red = +2.20 V vs. SCE), which undergoes a SET process with the N–H bond of 1 ( E ox = +1.86 V vs. SCE for 1a ) to generate nitrogen-centered radical A and the Mes-AcrPh˙ radical.…”

Carbofluorination of π‐Bonds and Related Reactions Involving Tandem C−C/C−F Bond Formation

“…Chen and Wu have recently disclosed a similar reaction of malonic acid derivatives, giving rise to β-fluoroesters, which replaces the Ag salt with an organic photoredox catalyst. [60] Scheme 18. Organocatalytic fluorinative semi-pinacol rearrangement of dihydropyrans.…”

Synthesis of ester-containing phenanthridinesviaphotoredox-catalyzed radical cascade cyclization ofN-arylacrylamides with alkyloxalyl chlorides

“…The yield was dramatically decreased when other organic and inorganic bases were used, such as 2-cyanopyridine, 1,4-diazabicyclo [2.2.2]octane (DABCO), K 2 HPO 4 , and K 2 CO 3 (entries 8-11). Control experiments demonstrated the necessity of 2-methylpyridine, the photocatalyst and light irradiation for this transformation (entries [12][13][14].…”

“…Recently, we have made significant progress in developing a series of cascade cyclization reactions of alkenes triggered by alkoxycarbonyl radicals, which has enabled us to construct a wide range of ester-containing heterocycles. 13 As part of our continuous efforts in the photocatalyzed alkoxycarbonylation of alkenes, 13,14 we used alkyloxalyl chlorides as the corresponding alkoxycarbonyl radical precursors, through the photoredox-catalyzed radical addition/nitrile insertion, followed by a radical cyclization to construct ester-substituted phenanthridines (Scheme 1c).…”