Tandem Gold(III)‐Catalyzed Amination‐Intramolecular Hydroamination Reactions of 1‐En‐4‐yn‐3‐ols with Sulfonamides: Efficient Approach to Highly Substituted Pyrroles

“…An elegant use of the gold‐promoted dehydrative amination reaction was reported by Liang and co‐workers for the synthesis of densely functionalized pyrroles 35 . The combined use of predesigned 1‐en‐4‐yn‐3‐ols 33 and HAuCl 4 ⋅ 4 H 2 O (20 mol %) led to NTs‐2,3,4,5‐tetrasubstituted pyrroles 35 in moderate to very high yields (up to 96 %).…”

Section: Allylic Substitutionsmentioning

confidence: 99%

Gold‐Catalyzed Allylation Reactions

Quintavalla

Bandini

2016

ChemCatChem

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The allylation reaction is a well‐established and indispensable tool for the development of chemical complexity and diversity in organic synthesis. Over several decades, this unique transformation has undergone several developments to establish a more simple, selective, and sustainable variant. Moving from stoichiometric amounts of metal additives to sub‐stoichiometric amounts, and more recently to catalytic loadings is only one of the chemical revolutions faced by the allylation reaction. In this context, homogeneous gold catalysis has played a pivotal role, resulting in unexpected reaction pathways, concerning unactivated unsaturated hydrocarbons, feasible. Among them, [AuI]‐ and [AuIII]‐assisted allylation reactions deserve particular mention owing to their impact in the synthesis of key organic building blocks and value‐added compounds. An unprecedented survey across the development of allylation methodologies based on this coinage metal is documented in the present Minireview.

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“…47 They had first reported the amination of 1-en-4-yn-3-ols. In this process, the propargylic alcohol unit was firstly activated by Au(III)-catalyst.…”

Section: Au-catalyzed Formation Of Pyrroles From Propargyl Alcoholsmentioning

confidence: 99%

Recent developments in the group-1B-metal-catalyzed synthesis of pyrroles

et al. 2016

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Pyrroles are important synthetic targets as a result of their occurrence in numerous biologically active molecules, their important roles in diverse living processes, and their utility as versatile intermediates. As a consequence, numerous efforts focused on the development of concise and efficient methods for the construction of pyrroles. Compared with other transition metals, the group 1B metals (Cu, Ag and Au) are probably more versatile and widely used for the synthesis of pyrroles in organic chemistry. Considering the importance of both topics in organic synthesis, here we summarize recent achievements in the synthesis of pyrroles catalyzed by monometallic systems which belong to the group 1B metals (Cu, Ag and Au).

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Tandem Gold(III)‐Catalyzed Amination‐Intramolecular Hydroamination Reactions of 1‐En‐4‐yn‐3‐ols with Sulfonamides: Efficient Approach to Highly Substituted Pyrroles

Cited by 90 publications

References 66 publications

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

Gold‐Catalyzed Allylation Reactions

Recent developments in the group-1B-metal-catalyzed synthesis of pyrroles

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