Synthesis 2024; 56(05): 751-757
DOI: 10.1055/a-2218-7534
feature

Cobalt Catalysis: C7 Alkynylation of Indolines with a Bromoalkyne

Manisha Manisha
a   C–H Activation & Phytochemistry Lab, Chemical Technology Division, CSIR-IHBT, Palampur, Himachal Pradesh, 176061, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India
,
Shiv Shankar Gupta
a   C–H Activation & Phytochemistry Lab, Chemical Technology Division, CSIR-IHBT, Palampur, Himachal Pradesh, 176061, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India
,
Upendra Sharma
a   C–H Activation & Phytochemistry Lab, Chemical Technology Division, CSIR-IHBT, Palampur, Himachal Pradesh, 176061, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India
› Author Affiliations
The research described in this manuscript is financially supported by the Council of Scientific and Industrial Research (CSIR) (MLP0203). M. and S.S.G. thank the University Grants Commission (UGC), New Delhi, and the CSIR, New Delhi, for senior research fellowships.


Abstract

A method for the cobalt-catalyzed C-7 alkynylation of indolines with (bromoethynyl)triisopropylsilane under mild conditions is described, leading to a diverse range of alkynylated indolines in good to excellent yields. Kinetic isotope studies indicate that the formation of a cobaltacycle might be the turnover-limiting step. Additionally, a gram-scale synthesis and oxidation of an indoline to an indole have been carried out successfully with excellent yields.

Supporting Information



Publication History

Received: 22 September 2023

Accepted after revision: 28 November 2023

Accepted Manuscript online:
28 November 2023

Article published online:
09 January 2024

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