-Hydroxyphthalimidyl Diazoacetate (NHPI-DA): a Modular Methylene Linchpin for the C-H Alkylation of Indoles

Overview

Journal Chem Commun (Camb)

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2021 May 6

PMID 33956022

Citations 2

Authors

Rajdip Chowdhury

Abraham Mendoza

Affiliations

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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.

Citing Articles

Modular Synthesis of (Borylmethyl)silanes through Orthogonal Functionalization of a Carbon Atom.

Chowdhury R, Elek G, Meana-Baamonde B, Mendoza A Org Lett. 2023; 25(11):1935-1940.

PMID: 36898045 PMC: 10043938. DOI: 10.1021/acs.orglett.3c00474.

Combined Experimental and Computational Study of Ruthenium -Hydroxyphthalimidoyl Carbenes in Alkene Cyclopropanation Reactions.

Planas F, Costantini M, Montesinos-Magraner M, Himo F, Mendoza A ACS Catal. 2021; 11(17):10950-10963.

PMID: 34504736 PMC: 8419840. DOI: 10.1021/acscatal.1c02540.

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