ChemInform Abstract: One‐Pot Synthesis of Substituted Benzo[b]furans and Indoles from Dichlorophenols/Dichloroanilines Using a Palladium—Dihydroxyterphenylphosphine Catalyst.

Yamaguchi, Miyuki; Akiyama, Tomoyo; Sasou, Hirohisa; Katsumata, Haruka; Manabe, Kei

doi:10.1002/chin.201647125

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“…Analogous to the sequence with dichlorophenols, Ntosyldichloroanilines 199 were also transformed to disubstituted indoles (200) using various terminal alkynes and boronic acids (Scheme 56B). 240,243 In addition to tosylated aniline derivatives, acetylated aniline derivatives were also suitable substrates for this transformation. Specifically, N-acetyl-2,4,6-trichloroaniline 201 reacted with various terminal alkynes to furnish a series of 2-substituted 5,7dichloroindoles (202).…”

Section: Ligand-binding Directing Groupsmentioning

confidence: 99%

Site-Selective Cross-Coupling of Polyhalogenated Arenes and Heteroarenes with Identical Halogen Groups

2021

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Methods to functionalize arenes and heteroarenes in a site-selective manner are highly sought after for rapidly constructing value-added molecules of medicinal, agrochemical, and materials interest. One effective approach is the site-selective cross-coupling of polyhalogenated arenes bearing multiple, but identical, halogen groups. Such cross-coupling reactions have proven to be incredibly effective for site-selective functionalization. However, they also present formidable challenges due to the inherent similarities in the reactivities of the halogen substituents. In this Review, we discuss strategies for site-selective cross-couplings of polyhalogenated arenes and heteroarenes bearing identical halogens, beginning first with an overview of the reaction types that are more traditional in nature, such as electronically, sterically, and directing-group-controlled processes. Following these examples is a description of emerging strategies, which includes ligand- and additive/solvent-controlled reactions as well as photochemically initiated processes.

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Section: Ligand-binding Directing Groupsmentioning

confidence: 99%