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^*

^*Corresponding author for this work

Chemistry

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

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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
Early online date	29 Aug 2024
DOIs	https://doi.org/10.1021/acs.orglett.4c02853
Publication status	E-pub ahead of print - 29 Aug 2024

Bibliographical note

PMC11406574

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10.1021/acs.orglett.4c02853Licence: Creative Commons: Attribution (CC BY)

MoreN2024RegiodivergentFinal published version, 1.72 MBLicence: Creative Commons: Attribution (CC BY)

A nitrenoid strategy to access sp3-rich nitrogen heterocycles
Davies, P. (Principal Investigator)
Engineering & Physical Science Research Council
1/05/22 → 30/09/25
Project: Research Councils
THIODIV: Exploring thioalkynes potential in gold catalysis with a divergent reactivity manifold
Davies, P. (Principal Investigator) & More, N. (Co-Investigator)
European Commission
21/10/20 → 20/10/22
Project: EU

Research data supporting the publication "Regiodivergent gold-catalyzed rearrangement-addition reactions of sulfenylated propargylic carboxylates with indoles"
More, N. (Creator), Gupta, A. (Creator), Rist, P. (Creator) & Davies, P. (Creator), University of Birmingham, 27 Aug 2024
DOI: 10.25500/edata.bham.00001161
Dataset

Cite this

@article{521e94be13524e3f916fd8ee2563d60a,

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.\}",

note = "PMC11406574",

year = "2024",

month = aug,

day = "29",

doi = "10.1021/acs.orglett.4c02853",

language = "English",

volume = "26",

pages = "7713--7717",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "36",

}

TY - JOUR

T1 - Regiodivergent Gold-Catalyzed Rearrangement–Addition Reactions of Sulfenylated Propargylic Carboxylates with Indoles

AU - More, Nagnath Y.

AU - Rist, Paige A.

AU - Gupta, Aniket

AU - Davies, Paul W.

N1 - PMC11406574

PY - 2024/8/29

Y1 - 2024/8/29

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.

U2 - 10.1021/acs.orglett.4c02853

DO - 10.1021/acs.orglett.4c02853

M3 - Letter

C2 - 39207898

SN - 1523-7060

VL - 26

SP - 7713

EP - 7717

JO - Organic Letters

JF - Organic Letters

IS - 36

ER -

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

Abstract

Bibliographical note

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Projects

A nitrenoid strategy to access sp3-rich nitrogen heterocycles

THIODIV: Exploring thioalkynes potential in gold catalysis with a divergent reactivity manifold

Datasets

Research data supporting the publication "Regiodivergent gold-catalyzed rearrangement-addition reactions of sulfenylated propargylic carboxylates with indoles"

Cite this