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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Selective Metalation and Functionalization of Fluorinated Nitriles Using 2,2,6,6-Tetramethylpiperidyl Bases

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Author(s):
dos Santos, Thiago [1] ; Orenha, Henrique P. [1] ; Murie, Valter E. [1] ; Vessecchi, Ricardo [1] ; Clososki, Giuliano C. [1]
Total Authors: 5
Affiliation:
[1] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Ciencias BioMol, BR-14040903 Ribeirao Preto, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: ORGANIC LETTERS; v. 23, n. 19, p. 7396-7400, OCT 1 2021.
Web of Science Citations: 0
Abstract

We have accomplished regioselective deprotometalation of aromatic and heteroaromatic nitriles via (TMP)(2)Zn center dot 2MgCl(2)center dot 2LiCl and TMPMgCl center dot LiCI (TMP = 2,2,6,6-tetramethylpiperidyl) with the exploration of new and scarcely investigated metalation positions. Regioselectivity was rationalized by DFT calculations. The quenching of the generated organozinc and organomagnesium intermediates with various electrophiles gave access to 47 highly functionalized nitriles with yields up to 95%. Additionally, we report a difunctionalization strategy and the use of functionalized nitriles as building blocks to construct relevant heterocycles. (AU)

FAPESP's process: 15/21364-6 - Applicantion of Organometallic Reagents in the Directed Functionalization of Quinolines Aimming the Synthesis of Medicinal Interest Compounds
Grantee:Valter Eduardo Murie
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 18/14150-8 - Selective aromatic functionalization: Methodological Studies and new applications in the synthesis of BIOATIVE compounds
Grantee:Giuliano Cesar Clososki
Support type: Regular Research Grants
FAPESP's process: 15/01017-0 - Multi-use instrument approved and awarded in the project 2013/50228-8, name of instrument: ultra-performance liquid chromatograph coupled with a high resolution mass spectrometer
Grantee:Roberto Gomes de Souza Berlinck
Support type: Multi-user Equipment Program