A trans diacyloxylation of indoles

Abstract

A trans diacyloxylation of indoles is accomplished by employing PhI(OAc)(2) as the oxidant. A broad range of functional groups are well tolerated. Both the electronic properties of the N-protecting groups of indoles and the acidity of the reaction media play important roles in the selectivity of indole acyloxylation reactions.

Ligand‐Promoted Palladium‐Catalyzed C−H Acetoxylation of Simple Arenes

“…After provingt he high activity of the new catalytic system in the CÀHa cetoxylation of benzene, we evaluated different substituteda renes ( Table 3). [16] PhI(OAc) 2 was used as the oxidant for all substrates and we comparedt he conditions without (conditions A) or with 6-fluoropicolinic acid (conditions B) for each substrate.…”

Functionalization of Carborane via Carboryne Intermediates

“…When R = aryl groups, both III-B and III-C are formed. Such III-C/III-B ratios increase if an electron-withdrawing substituent is introduced to the phenyl ring, which may be ascribed to the increased electrophilicity of C2 position in the intermediate III-A [25].…”

“…Further optimization of the reaction conditions found that both temperature and reaction time are crucial to the yields of the product. High temperatures or prolonged reaction time dramatically decreased the yields, probably due to the deboronation of the product by fluoride (Table 4.1, entries 1-4) [25]. The reaction medium also displayed significant influence on the outcome of this reaction.…”

“…Similar to the aromatic benzene systems, nucleophilic substitution reaction also proceeds well in the case of o-carboranes that bearing excellent boron leaving groups, such as N 2 + and PhI + substituents (Scheme 1.4) [25][26][27][28]. …”

An Aluminum Triflate‐Catalyzed Intramolecular Reaction Sequence Toward Concise Construction of the Tetrahydropyrido[1,2‐a]indol‐6‐one Skeleton

“…The high yield of 2n in Table 2 also points to this conclusion. That is to say, the tendency of protonation on the C‐3 position decides whether the reaction can proceed smoothly 12. Besides, a metal center of the complexed intermediate was crucial.…”