Synthesis of <scp><i>N</i></scp>‐Hydroxyindole Derivatives via Pd‐Catalyzed Electrophilic Cyclization

Oh, Soo Min; Shin, Seunghoon

doi:10.1002/bkcs.12285

Cited by 3 publications

(1 citation statement)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The requisite N -hydroxyindole derivatives were synthesized according to the literature. 20 Particularly, for the C2-substituted N -hydroxyindoles used in this study, a sequence comprising Sonogashira coupling of o -halonitrobenzenes, partial reduction into hydroxylamines, and Larock-type cyclization, were found general. 20 d With an N -carboxyindole 1a and 3,5-dimethoxyphenol 2a as prototypical substrates, we set out to explore the possibility of a non-metal catalyzed C–H/C–H coupling, employing various Brønsted acids (entries 1–6, Table 1 ).…”

Section: Resultsmentioning

confidence: 75%

Ortho-selective C–H arylation of phenols with N-carboxyindoles under Brønsted acid- or Cu(i)-catalysis

Nguyen

Park

et al. 2022

Chem. Sci.

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 75%

Ortho-selective C–H arylation of phenols with N-carboxyindoles under Brønsted acid- or Cu(i)-catalysis

Nguyen

Park

et al. 2022

Chem. Sci.

Self Cite

View full text Add to dashboard Cite

show abstract

Energy Transfer Photocatalytic Radical Rearrangement in N-Indolyl Carbonates

Bera

Hwang

et al. 2022

Org. Lett.

Self Cite

View full text Add to dashboard Cite

A new type of sp3-like N-centered radical has been generated by selective energy transfer catalysis. Upon photoexcitation, homolytic N–O bond cleavage of N-indolyl carbonate in the presence of an Ir complex produced N- and O-centered radicals. The high spin density at the C3 position of indole led to radical recombination with the O-centered radical, affording valuable 3-oxyindole derivatives without decarboxylation. Transformations of the desired products into various molecules were also demonstrated.

show abstract

One-Pot Synthesis of 2-Sulfonamidobenzo[b]thiophenes Enabled by a Mild Protonative Activation of Ynamides

et al. 2022

View full text Add to dashboard Cite

The silica gel- or solvent-promoted intramolecular protonative cyclization of ynamides containing o-methylthioaryl groups resulted in the one-pot formation of biologically important benzo[b]thiophenes. Compared with ynamide activation methods that use strong Brønsted acids or expensive transition metals, this protocol is mild and economical. Due to these merits, various functionalized 2-amido benzo[b]thiophenes were furnished in a convenient way.

show abstract

Synthesis of N‐Hydroxyindole Derivatives via Pd‐Catalyzed Electrophilic Cyclization

Abstract: A synthetic protocol for the synthesis of C2‐substituted N‐hydroxyindoles has been developed which consists of Sonogashira coupling, partial reduction of the nitro group, and Larock cyclization. This protocol features superior generality and efficiency over conventional alternatives.

Cited by 3 publications

References 18 publications

Ortho-selective C–H arylation of phenols with N-carboxyindoles under Brønsted acid- or Cu(i)-catalysis

Ortho-selective C–H arylation of phenols with N-carboxyindoles under Brønsted acid- or Cu(i)-catalysis

Energy Transfer Photocatalytic Radical Rearrangement in N-Indolyl Carbonates

One-Pot Synthesis of 2-Sulfonamidobenzo[b]thiophenes Enabled by a Mild Protonative Activation of Ynamides

Contact Info

Product

Resources

About