Regiodivergent Gold-Catalyzed Rearrangement-Addition Reactions of Sulfenylated Propargylic Carboxylates with Indoles

Nagnath Y. More; Paige A. Rist; Aniket Gupta; Paul W. Davies

doi:10.1021/acs.orglett.4c02853

Regiodivergent Gold-Catalyzed Rearrangement-Addition Reactions of Sulfenylated Propargylic Carboxylates with Indoles

Nagnath Y. More, Paige A. Rist, Aniket Gupta, Paul W. Davies

Research output: Contribution to journal › Article › peer-review

Abstract

Sulfenylated propargylic carboxylates were introduced to investigate the influence of sulfur substitution in gold-catalyzed alkyne activation pathways. Regiodivergent gold-catalyzed rearrangement and indole capture reactions proceed under mild conditions to give functionalized indole products bearing sulfenylated (Z)-enol carboxylate motifs. Pathways involving both 1,2- and 1,3-carboxylate migrations are achieved selectively, with indole being added in a 1,4 relationship to the sulfenyl group in each case. High levels of selectivity are influenced by the catalyst system, counterion, and carboxylate group.

Original language	English
Pages (from-to)	7713-7717
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	36
DOIs	https://doi.org/10.1021/acs.orglett.4c02853
State	Published - 13 Sep 2024
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Regiodivergent Gold-Catalyzed Rearrangement-Addition Reactions of Sulfenylated Propargylic Carboxylates with Indoles",

abstract = "Sulfenylated propargylic carboxylates were introduced to investigate the influence of sulfur substitution in gold-catalyzed alkyne activation pathways. Regiodivergent gold-catalyzed rearrangement and indole capture reactions proceed under mild conditions to give functionalized indole products bearing sulfenylated (Z)-enol carboxylate motifs. Pathways involving both 1,2- and 1,3-carboxylate migrations are achieved selectively, with indole being added in a 1,4 relationship to the sulfenyl group in each case. High levels of selectivity are influenced by the catalyst system, counterion, and carboxylate group.",

author = "More, {Nagnath Y.} and Rist, {Paige A.} and Aniket Gupta and Davies, {Paul W.}",

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AU - Rist, Paige A.

AU - Gupta, Aniket

AU - Davies, Paul W.

PY - 2024/9/13

Y1 - 2024/9/13

N2 - Sulfenylated propargylic carboxylates were introduced to investigate the influence of sulfur substitution in gold-catalyzed alkyne activation pathways. Regiodivergent gold-catalyzed rearrangement and indole capture reactions proceed under mild conditions to give functionalized indole products bearing sulfenylated (Z)-enol carboxylate motifs. Pathways involving both 1,2- and 1,3-carboxylate migrations are achieved selectively, with indole being added in a 1,4 relationship to the sulfenyl group in each case. High levels of selectivity are influenced by the catalyst system, counterion, and carboxylate group.

AB - Sulfenylated propargylic carboxylates were introduced to investigate the influence of sulfur substitution in gold-catalyzed alkyne activation pathways. Regiodivergent gold-catalyzed rearrangement and indole capture reactions proceed under mild conditions to give functionalized indole products bearing sulfenylated (Z)-enol carboxylate motifs. Pathways involving both 1,2- and 1,3-carboxylate migrations are achieved selectively, with indole being added in a 1,4 relationship to the sulfenyl group in each case. High levels of selectivity are influenced by the catalyst system, counterion, and carboxylate group.

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 36

ER -

Regiodivergent Gold-Catalyzed Rearrangement-Addition Reactions of Sulfenylated Propargylic Carboxylates with Indoles

Abstract

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