Iron nitrate and 4-OH-TEMPO-cocatalyzed aerobic oxidation of isochromans

Abstract

An efficient aerobic oxidation of isochromans and their derivatives with Fe(NO3)3•9H2O and 4-OH-TEMPO as catalysts at room temperature has been developed. The method provides a convenient approach to synthesize the...

A simple and convenient strategy for the oxidation of C(sp3)–H bonds based on γ-valerolactone

“…Mechanistically, hydrogen atom transfer (HAT) is an important pathway for activating C(sp 3 )-H bonds [1][2][3] and has thus attracted considerable research attention. Various reaction systems for C(sp 3 )-H bond activation have been developed based on N-oxyl compounds, [4][5][6][7] peroxides, 8,9 disulfides 10,11 and halogen species, 12,13 amides, 14,15 and CBrCl 3 analogues, 16,17 among others, providing reactive O, S, X (X = Cl, Br, I), N-centered, and C-centered radicals as hydrogen atom abstractors. However, most of these compounds are consumed in the reaction, and more than one equiv.…”

Iron-catalyzed selective construction of indole derivatives via oxidative C(sp3)–H functionalization of indolin-2-ones

“…[1][2][3][4][5][6][7][8][9][10][11] Inspired by iron-containing enzyme catalysis, 12,13 the iron-catalyzed C(sp 3 )-H bond oxidation, coupled with the utilization of molecular oxygen, has emerged as a highly promising reaction over the past decade. [14][15][16][17][18][19][20][21][22][23][24] In 2015, Li's group pioneered the utilization of cross-dehydrogenative coupling (CDC) to develop an iron saltcatalyzed cross-dehydrogenative arylation between 3-substituted indolin-2-ones generating a series of 3,3′-disubstituted oxindole compounds. 25 Subsequently, Xu's group achieved significant progress by expanding the scope of the iron-catalyzed CDC reaction to include indolin-2-ones and various X-H bonds (X = C, N, or S), enabling the construction of functionalized indole derivatives by employing air as the sole oxidant (Scheme 1(I)).…”

Oxidations of Alcohols, Aldehydes, and Diols Using NaBr and Selectfluor

“…Characterization data matches the literature. 99 Compound 75. using the General Procedure on a 0.5 mmol scale using 3 equiv of Selectfluor and 3 equiv of NaBr in a 1:1 mixture of CH 3 CN/H 2 O for 19 h; Purified using a gradient of 10 to 20% EtOAc/hexanes on silica gel (white solid, 0.065 g, 0.284 mmol, 57% yield). 1 H NMR (400 MHz, CDCl 3 ) δ 10.18 (s, 1H), 7.36 (s, 1H), 7.06 (s, 1H), 6.08 (s, 2H).…”