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The transformation of alcohols to important classes of compounds is a central topic in chemistry because they are abundant, renewable, and attractive building blocks. The alkali‐mediated/catalyzed borrowing hydrogen and aerobic dehydrogenation processes of alcohols open a new and sustainable access for the alcohol conversion under transition‐metal‐free conditions. In this review, we summarize the recent alkali‐mediated/catalyzed sequential reactions involving the borrowing hydrogen and aerobic dehydrogenation processes of alcohols. Furthermore, this review not only introduces the tentative pathways of these transformations, but also discusses the role of alkali, solvent effects, and substrate reactivity on these reactions. [ABSTRACT FROM AUTHOR]

We report an electrochemically promoted decarboxylation of readily available carboxylic acid and subsequent Mumm rearrangement to synthesize the corresponding imides. The reaction features external oxidant‐free, transition metal‐free mild conditions, and good functional group tolerance, affording various imides in moderate to good yields. Mechanistic studies reveal that the selective oxidation of aliphatic carboxylic acids appears to be the key step in this transformation. [ABSTRACT FROM AUTHOR]

Indole motifs are important heterocycles found in natural products, pharmaceuticals, agricultural chemicals, and materials. Although there are well-established classical name reactions for indole synthesis, these transformations often require harsh reaction conditions, have a limited substrate scope, and exhibit poor regioselectivity. As a result, organic synthesis chemists have been exploring efficient and practical methods, leading to numerous strategies for synthesizing a variety of functionalized indoles. In recent years, electrochemistry has emerged as an environmentally friendly and sustainable synthetic tool, with widespread applications in organic synthesis. This technology allows for elegant synthetic routes to be developed for the construction of indoles under external oxidant-free conditions. This feature article specifically focuses on recent advancements in indole synthesis from non-indole-based substrates, as well as the mechanisms underlying these transformations. [ABSTRACT FROM AUTHOR]

A simple protocol for amide bond construction using β‐keto sulfonyl fluorides (BKSFs) as the acyl surrogates has been achieved. The reaction of BKSFs with a range of amines could be performed in presence of N‐bromosuccinimide (NBS), affording various amides with diverse functionalities. Preliminary mechanistic studies revealed that the dibromo‐substituted sulfonyl fluorides could be the key intermediate in this amidation process. [ABSTRACT FROM AUTHOR]

A series of tryptamine derivatives were transformed into their corresponding 3‐chloro‐2‐oxidation products under simple and mild conditions. This protocol is an operationally simple system that utilizes a single reagent SO2ClF plays a dual role as both oxidant and chloride source and enables the construction of various 3,3‐disubstituted oxindoles with good functional group tolerance. The transformations of the product highlight its potential synthetic applications. [ABSTRACT FROM AUTHOR]

Keywords: organic electrochemistry; indoles; 3-sulfonylindoles; oxidation; sodium sulfinates; alkynylanilines EN organic electrochemistry indoles 3-sulfonylindoles oxidation sodium sulfinates alkynylanilines 2959 2968 10 08/31/23 20230915 NES 230915 Graph Indoles exist ubiquitously in pharmaceuticals, agrochemicals, and natural products, and are among the most important nitrogen-containing heterocycles. HRMS-ESI: I m i / I z i [M + Na] SP + sp calcd for C SB 29 sb H SB 22 sb N SB 2 sb O SB 4 sb S SB 2 sb Na: 549.0913; found: 549.0915. HRMS-ESI: I m i / I z i [M + Na] SP + sp calcd for C SB 28 sb H SB 20 sb N SB 2 sb O SB 4 sb S SB 2 sb Na: 535.0757; found: 535.0753. HRMS-ESI: I m i / I z i [M + Na] SP + sp calcd for C SB 29 sb H SB 22 sb F SB 3 sb NO SB 4 sb S SB 2 sb Na: 592.0835; found: 592.0839. [Extracted from the article]