Silver-catalyzed tandem hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1 '-allylspiro[indene-1,2 '-indolin]-3 '-ones

Srinivasa Reddy Mothe; Maria Laurentia Novianti; Benjamin James Ayers; Philip Wai Hong Chan

doi:10.1021/ol501809p

Silver-catalyzed tandem hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1 '-allylspiro[indene-1,2 '-indolin]-3 '-ones

Srinivasa Reddy Mothe, Maria Laurentia Novianti, Benjamin James Ayers, Philip Wai Hong Chan

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

33 Citations (Scopus)

Abstract

An efficient silver triflate-catalyzed tandem hydroamination/hydroarylation cascade generating 1′- allylspiro[indene-1,2′-indolin]-3′-ones from 1-(2-allylamino)- phenyl-4-hydroxy-but-2-yn-1-ones is described. The reaction conditions are mild and general in scope and proceed to highly functionalized spiro-targets in high yield. This novel class of molecule possesses both the privileged indene and indolin-3- one scaffold, which may lead to possible pharmacological applications.

Original language	English
Pages (from-to)	4110 - 4113
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	16
DOIs	https://doi.org/10.1021/ol501809p
Publication status	Published - 2014
Externally published	Yes

Keywords

Gold
gold catalysis
Catalysis

Cite this

Mothe, S. R., Novianti, M. L., Ayers, B. J., & Chan, P. W. H. (2014). Silver-catalyzed tandem hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1 '-allylspiro[indene-1,2 '-indolin]-3 '-ones. Organic Letters, 16(16), 4110 - 4113. https://doi.org/10.1021/ol501809p

Mothe, Srinivasa Reddy ; Novianti, Maria Laurentia ; Ayers, Benjamin James ; Chan, Philip Wai Hong. / Silver-catalyzed tandem hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1 '-allylspiro[indene-1,2 '-indolin]-3 '-ones. In: Organic Letters. 2014 ; Vol. 16, No. 16. pp. 4110 - 4113.

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title = "Silver-catalyzed tandem hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1 '-allylspiro[indene-1,2 '-indolin]-3 '-ones",

abstract = "An efficient silver triflate-catalyzed tandem hydroamination/hydroarylation cascade generating 1′- allylspiro[indene-1,2′-indolin]-3′-ones from 1-(2-allylamino)- phenyl-4-hydroxy-but-2-yn-1-ones is described. The reaction conditions are mild and general in scope and proceed to highly functionalized spiro-targets in high yield. This novel class of molecule possesses both the privileged indene and indolin-3- one scaffold, which may lead to possible pharmacological applications.",

keywords = "Gold, gold catalysis, Catalysis",

author = "Mothe, {Srinivasa Reddy} and Novianti, {Maria Laurentia} and Ayers, {Benjamin James} and Chan, {Philip Wai Hong}",

year = "2014",

doi = "10.1021/ol501809p",

language = "English",

volume = "16",

pages = "4110 -- 4113",

journal = "Organic Letters",

issn = "1523-7060",

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Mothe, SR, Novianti, ML, Ayers, BJ & Chan, PWH 2014, 'Silver-catalyzed tandem hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1 '-allylspiro[indene-1,2 '-indolin]-3 '-ones', Organic Letters, vol. 16, no. 16, pp. 4110 - 4113. https://doi.org/10.1021/ol501809p

Silver-catalyzed tandem hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1 '-allylspiro[indene-1,2 '-indolin]-3 '-ones. / Mothe, Srinivasa Reddy; Novianti, Maria Laurentia; Ayers, Benjamin James; Chan, Philip Wai Hong.

In: Organic Letters, Vol. 16, No. 16, 2014, p. 4110 - 4113.

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

TY - JOUR

T1 - Silver-catalyzed tandem hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1 '-allylspiro[indene-1,2 '-indolin]-3 '-ones

AU - Mothe, Srinivasa Reddy

AU - Novianti, Maria Laurentia

AU - Ayers, Benjamin James

AU - Chan, Philip Wai Hong

PY - 2014

Y1 - 2014

N2 - An efficient silver triflate-catalyzed tandem hydroamination/hydroarylation cascade generating 1′- allylspiro[indene-1,2′-indolin]-3′-ones from 1-(2-allylamino)- phenyl-4-hydroxy-but-2-yn-1-ones is described. The reaction conditions are mild and general in scope and proceed to highly functionalized spiro-targets in high yield. This novel class of molecule possesses both the privileged indene and indolin-3- one scaffold, which may lead to possible pharmacological applications.

AB - An efficient silver triflate-catalyzed tandem hydroamination/hydroarylation cascade generating 1′- allylspiro[indene-1,2′-indolin]-3′-ones from 1-(2-allylamino)- phenyl-4-hydroxy-but-2-yn-1-ones is described. The reaction conditions are mild and general in scope and proceed to highly functionalized spiro-targets in high yield. This novel class of molecule possesses both the privileged indene and indolin-3- one scaffold, which may lead to possible pharmacological applications.

KW - Gold

KW - gold catalysis

KW - Catalysis

U2 - 10.1021/ol501809p

DO - 10.1021/ol501809p

M3 - Article

VL - 16

SP - 4110

EP - 4113

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

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Mothe SR, Novianti ML, Ayers BJ, Chan PWH. Silver-catalyzed tandem hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1 '-allylspiro[indene-1,2 '-indolin]-3 '-ones. Organic Letters. 2014;16(16):4110 - 4113. https://doi.org/10.1021/ol501809p

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10.1021/ol501809p