Difluoromethylborates and Muonium for the Study of Isonitrile Insertion Affording Phenanthridines via Imidoyl Radicals.

Kakeru Konagaya, Yu-En Huang, Kazuki Iwami, Tetsuya Fujino, Rikutaro Abe, Reuben Parchment-Morrison, Kenji M Kojima, Iain McKenzie, Shigekazu Ito

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Article in The Journal of organic chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

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4 · The record

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5 · Who and what money

Authors and funding

9 authors.

Kakeru KonagayaDepartment of Applied Chemistry, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-H-113 Ookayama, Meguro-ku, Tokyo 152-8552, Japan.

Yu-En HuangDepartment of Applied Chemistry, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-H-113 Ookayama, Meguro-ku, Tokyo 152-8552, Japan.

Kazuki IwamiDepartment of Applied Chemistry, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-H-113 Ookayama, Meguro-ku, Tokyo 152-8552, Japan.

Tetsuya FujinoDepartment of Applied Chemistry, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-H-113 Ookayama, Meguro-ku, Tokyo 152-8552, Japan.

Rikutaro AbeDepartment of Applied Chemistry, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-H-113 Ookayama, Meguro-ku, Tokyo 152-8552, Japan.

Reuben Parchment-MorrisonSchool of Physics and Astronomy, Cardiff University, Queen's Building, The Parade, Cardiff CF24 3AA, U.K.

Kenji M KojimaCentre for Molecular and Materials Science, TRIUMF, 4004 Wesbrook Mall, Vancouver, British Columbia V6T 2A3, Canada.

Iain McKenzieCentre for Molecular and Materials Science, TRIUMF, 4004 Wesbrook Mall, Vancouver, British Columbia V6T 2A3, Canada.

Shigekazu ItoDepartment of Applied Chemistry, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-H-113 Ookayama, Meguro-ku, Tokyo 152-8552, Japan.ORCID 0000-0002-5737-8499

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The 6-(difluoromethyl)phenanthridine unit is a highly attractive fluoroalkyl-substituted planar nitrogen heterocycle in pharmaceutical and agrochemical research. In this paper, we report that difluoromethylborates can be used as a source of difluoromethyl radicals for isonitrile insertion, leading to 6-(difluoromethyl)phenanthridines. Tuning the aryl substituents in the difluoromethylborates and oxidizing reagents enabled the synthesis of 6-(difluoromethyl)phenanthridines through the generation of difluoromethyl radical and spontaneous intramolecular cyclization of the CF

Identifiers

PMID37351949

DOI10.1021/acs.joc.3c00056

PMCPMC10337039

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