Hydroformylation of 2-Alkynylanilines: Toward an Alternative Methodology for the Synthesis of 3-Substituted Indoles

Cedric Holzapfel; Etelinda Dasilva; Laetitia Den Drijver; Tyler Bredenkamp

doi:10.1002/cctc.201600659

Hydroformylation of 2-Alkynylanilines: Toward an Alternative Methodology for the Synthesis of 3-Substituted Indoles

Cedric Holzapfel
, Etelinda Dasilva
, Laetitia Den Drijver
, Tyler Bredenkamp

Chemical Sciences

University of Johannesburg

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

4 Citations (Scopus)

Abstract

A potentially viable route for the synthesis of 3-substituted indoles is presented herein. The methodology is based on a regioselective Rh-catalysed hydroformylation of prepared 2-alkyn-1-ylanilines. The requisite 2-alkynylaniline substrates were prepared in high yields (>85 %) using the Pd-catalysed Sonogashira reaction. A catalyst complex that comprises Rh^I(CO)(PPh₃)₃ and 1,2-bis(diphenylphosphino)ethane as the ligand allowed the quantitative conversions of the alkynyl substrates with selectivities >75 % for the desired 3-substituted indoles.

Original language	English
Pages (from-to)	2912-2915
Number of pages	4
Journal	ChemCatChem
Volume	8
Issue number	18
DOIs	https://doi.org/10.1002/cctc.201600659
Publication status	Published - 21 Sept 2016

Keywords

alkynes
hydroformylation
regioselectivity
rhodium
synthesis design

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1002/cctc.201600659

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title = "Hydroformylation of 2-Alkynylanilines: Toward an Alternative Methodology for the Synthesis of 3-Substituted Indoles",

abstract = "A potentially viable route for the synthesis of 3-substituted indoles is presented herein. The methodology is based on a regioselective Rh-catalysed hydroformylation of prepared 2-alkyn-1-ylanilines. The requisite 2-alkynylaniline substrates were prepared in high yields (>85 \%) using the Pd-catalysed Sonogashira reaction. A catalyst complex that comprises RhI(CO)(PPh3)3 and 1,2-bis(diphenylphosphino)ethane as the ligand allowed the quantitative conversions of the alkynyl substrates with selectivities >75 \% for the desired 3-substituted indoles.",

keywords = "alkynes, hydroformylation, regioselectivity, rhodium, synthesis design",

author = "Cedric Holzapfel and Etelinda Dasilva and \{Den Drijver\}, Laetitia and Tyler Bredenkamp",

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T1 - Hydroformylation of 2-Alkynylanilines

T2 - Toward an Alternative Methodology for the Synthesis of 3-Substituted Indoles

AU - Holzapfel, Cedric

AU - Dasilva, Etelinda

AU - Den Drijver, Laetitia

AU - Bredenkamp, Tyler

PY - 2016/9/21

Y1 - 2016/9/21

N2 - A potentially viable route for the synthesis of 3-substituted indoles is presented herein. The methodology is based on a regioselective Rh-catalysed hydroformylation of prepared 2-alkyn-1-ylanilines. The requisite 2-alkynylaniline substrates were prepared in high yields (>85 %) using the Pd-catalysed Sonogashira reaction. A catalyst complex that comprises RhI(CO)(PPh3)3 and 1,2-bis(diphenylphosphino)ethane as the ligand allowed the quantitative conversions of the alkynyl substrates with selectivities >75 % for the desired 3-substituted indoles.

AB - A potentially viable route for the synthesis of 3-substituted indoles is presented herein. The methodology is based on a regioselective Rh-catalysed hydroformylation of prepared 2-alkyn-1-ylanilines. The requisite 2-alkynylaniline substrates were prepared in high yields (>85 %) using the Pd-catalysed Sonogashira reaction. A catalyst complex that comprises RhI(CO)(PPh3)3 and 1,2-bis(diphenylphosphino)ethane as the ligand allowed the quantitative conversions of the alkynyl substrates with selectivities >75 % for the desired 3-substituted indoles.

KW - alkynes

KW - hydroformylation

KW - regioselectivity

KW - rhodium

KW - synthesis design

UR - https://www.scopus.com/pages/publications/84988329934

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DO - 10.1002/cctc.201600659

M3 - Article

AN - SCOPUS:84988329934

SN - 1867-3880

VL - 8

SP - 2912

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JO - ChemCatChem

JF - ChemCatChem

IS - 18

ER -

Hydroformylation of 2-Alkynylanilines: Toward an Alternative Methodology for the Synthesis of 3-Substituted Indoles

Abstract

Keywords

ASJC Scopus subject areas

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