Light-accelerated “on-water” hydroacylation of dialkyl azodicarboxylates

Abstract

Organic synthesis is in a continuous lookout for the development of novel organic reactions or the improvement of traditional organic transformations. The hydroacylation of dialkyl azodicarboxylates has received a lot...

Total Synthesis and Bioactivity Profile of (+)-Ieodomycins A and B and their Stereoisomers

“…1 H NMR (500 MHz, CDCl 3 ) δ 9.80 (t, J = 1.8 Hz, 1H), 7.37–7.27 (m, 5H), 4.53 (s, 2H), 3.81 (t, J = 6.1 Hz, 2H), 2.70 (dt, J = 6.1, 1.8 Hz, 2H); 13 C­{ 1 H} NMR (125 MHz, CDCl 3 ) δ 201.3, 137.9, 128.5, 127.9, 127.8, 73.4, 63.9, 44.0; HRMS (ESI) for C 10 H 12 O 2 Na [M + Na] + calcd 187.0735, found 187.0733. Data are consistent with those reported in the literature …”

“…Data are consistent with those reported in the literature. 30 (S)-1-(Benzyloxy)hex-5-en-3-ol (7a). To a solution of (S)-BINOL (214.4 mg, 0.749 mmol, 0.1 equiv) in DCM (7.5 mL), 4 Å molecular sieves (3.28 g) were added.…”

Metal-free C(sp3)–H functionalization (C–C and C–N bond formation) of 1,2,3,4-tetrahydroacridines using deep eutectic solvents as catalyst and reaction medium

“…6 Besides this, dialkyl azodicarboxylates are used as electrophiles for C–N bond formation reactions via nucleophilic addition. 7–9 In this connection, Guo 3 and the Hung 5 groups reported transition metal catalysed amination of the un-activated C(sp 3 )–H bond of 2-alkyl azaarenes using diethyl azodicarboxylate. Similarly, Saget and co-workers also reported Zn-ProPhenol catalysed amination of un-activated aryl and vinyl ketones with di- tert -butyl azodicarboxylate.…”

Photoredox-Catalyzed Hydroacylation of Azobenzenes with Carboxylic Acids

“…More recently, the Stoltz group reported the N–N coupling of O -benzoylated hydroxamates with a broad range of aryl and aliphatic amines via nickel catalysis to form acyl hydrazides . The synthesis of acyl hydrazide scaffolds by C–N bond coupling was realized by addition of aldehydes to azodicarboxylates, which are reactive azo anologues known as excellent radical/ionic-based nucleophile acceptors with low-energy LUMO . On the contrary, the hydroacylation of azobenzenes has been much less developed.…”