Issue 37, 2021
From the journal:

Chemical Communications

N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C–H alkylation of indoles†

Rajdip Chowdhury ORCID logo a  and  Abraham Mendoza ORCID logo *a  

* Corresponding authors

a Department of Organic Chemistry, Arrhenius laboratory, Stockholm University, 106 91 Stockholm, Sweden
E-mail: abraham.mendoza@su.se

Abstract

Despite the extensive studies on the reactions between conventional diazocompounds and indoles, these are still limited by the independent synthesis of the carbene precursors, the specific catalysts, and the required multi-step manipulation of the products. In this work, we explore redox-active carbenes in the expedited and divergent synthesis of functionalized indoles. NHPI-DA displays unusual efficiency and selectivity to yield insertion products that can be swiftly elaborated into boron and carbon substituents that are particularly problematic in carbene-mediated reactions.

Graphical abstract: N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C–H alkylation of indoles

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Article information

DOI
https://doi.org/10.1039/D1CC01026C
Article type
Communication
Submitted
12 Mar 2021
Accepted
29 Mar 2021
First published
29 Mar 2021
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2021,57, 4532-4535

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N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C–H alkylation of indoles

R. Chowdhury and A. Mendoza, Chem. Commun., 2021, 57, 4532 DOI: 10.1039/D1CC01026C

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