Iron-catalyzed domino coupling reactions of π-systems

• Austin Pounder and
• William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

• action of Meerwein’s salt (Me3OBF4) and a mild base (proton sponge) to afford a methoxy cedrene derivative. Next, oxidative cleavage of the double bond using NaIO4/RuCl3·xH2O enabled a ring opening, followed by lactonization promoted by CuBr2 via an intramolecular acyloxylation. The 5,5-fused ring system

Transition-metal-catalyzed synthesis of phenols and aryl thiols

• Yajun Liu,
• Shasha Liu and
• Yan Xiao

Beilstein J. Org. Chem. 2017, 13, 589–611, doi:10.3762/bjoc.13.58

• the chlorination and other C–H functionalization of (2-pyridyl)arenes. Together with this work, some other work on C–H acyloxylation provided an indirect pathway for the synthesis of phenols from arenes [54]. In 2014, Shi and co-workers designed a removable bidentate functional group, which could

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

• Igor B. Krylov,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

• reactions of CH- and OH-reagents, closely related C–H activation processes involving intermolecular C–O bond formation are discussed: acyloxylation reactions with ArI(O2CR)2 reagents and generation of O-reagents in situ from C-reagents (methylarenes, aldehydes, etc.). Keywords: acyloxylation; alkoxylation

• acids are most commonly used as O-reagents; hydroxylamine derivatives, hydroperoxides, and sulfonic acids are employed less frequently. In the case of O-reagent PhI(O2CR)2, dehydrogenated carboxylic acid RCO2H is preliminary included in the oxidant, so C–H acyloxylation with PhI(O2CR)2 can be considered

• = F (Scheme 3). The pyridine moiety served as the directing group in many works to accomplish the ortho-acyloxylation of arenes 4 giving products 5 (Table 1). The reactions were catalyzed by copper, palladium, or rhodium salts. Carboxylic acids or their salts, as well as aldehydes, methylarenes

Synthesis and antibacterial activity of monocyclic 3-carboxamide tetramic acids

• Yong-Chul Jeong and
• Mark G. Moloney

Beilstein J. Org. Chem. 2013, 9, 1899–1906, doi:10.3762/bjoc.9.224

• -hydroxysuccinimide esters of N-acetylamino acids has been reported [19], we wished to exploit an alternative approach based upon C-acyloxylation of enolates followed by amine exchange, which had been shown to be very effective in a pyroglutamate series, since it offered synthetic simplicity and the potential for

Palladium-catalyzed dual C–H or N–H functionalization of unfunctionalized indole derivatives with alkenes and arenes

• Gianluigi Broggini,
• Egle M. Beccalli,
• Andrea Fasana and
• Silvia Gazzola

Beilstein J. Org. Chem. 2012, 8, 1730–1746, doi:10.3762/bjoc.8.198

• reaction [85]. A mild cyclization of 2-alkenylindoles 53 involving an alkenylation/acyloxylation process resulted in the formation of the 1,2,3,4-tetrahydrocarbazoles 54 bearing oxygen-containing functionalized groups (Scheme 31) [86]. Reactions were carried out by using 1,4-benzoquinone as the oxidizing

• /esterification process through iminium intermediates. Cyclization of 3-indolylallylcarboxamides involving 1,2-migration of the acyl group from spiro-intermediates. Domino reactions of 2-indolylallylcarboxamides involving N–H functionalization. Cyclization/acyloxylation reaction of 3-alkenylindoles. Doubly

Enantioselective total synthesis of (R)-(−)-complanine

• Krystal A. D. Kamanos and
• Jonathan M. Withey

Beilstein J. Org. Chem. 2012, 8, 1695–1699, doi:10.3762/bjoc.8.192

• ). Although a number of acyloxylations have been reported, the direct catalytic asymmetric acyloxylation of aldehydes has only been recently realized [6][7]. Thus, the asymmetric benzoylation of aldehydes, according to the method of Tomkinson [7], was attempted. Utilizing benzoyl peroxide in the presence of