Mechanistic Studies on the Synthesis of Pyrrolidines and Piperidines via Copper-Catalyzed Intramolecular C-H Amination

José María Muñoz-Molina; Daniel Bafaluy; Ignacio Funes-Ardoiz; Adiran De Aguirre; Feliu Maseras; Tomás R. Belderrain; Pedro J. Pérez; Kilian Muñiz

doi:10.1021/acs.organomet.2c00095

Mechanistic Studies on the Synthesis of Pyrrolidines and Piperidines via Copper-Catalyzed Intramolecular C-H Amination

José María Muñoz-Molina, Daniel Bafaluy, Ignacio Funes-Ardoiz, Adiran De Aguirre, Feliu Maseras, Tomás R. Belderrain^*, Pedro J. Pérez, Kilian Muñiz

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Departament de Química

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Resum

We have recently developed a method for the synthesis of pyrrolidines and piperidines via intramolecular C-H amination of N-fluoride amides using [TpxCuL] complexes as precatalysts [Tpx = tris(pyrazolyl)borate ligand and L = THF or CH3CN]. Herein, we report mechanistic studies on this transformation, which includes the isolation and structural characterization of a fluorinated copper(II) complex, [(TpiPr2OH)CuF] [TpiPr = hydrotris(3,5-diisopropylpyrazolyl)borate], pertinent to the mechanistic pathway. The effects of the nature of the Tpx ligand in the copper catalyst as well as of the halide in the N-X amides employed as reactants have been investigated both from experimental and computational perspectives.

Idioma original	Anglès
Pàgines (de-a)	1099-1105
Nombre de pàgines	7
Revista	Organometallics
Volum	41
Número	9
DOIs	https://doi.org/10.1021/acs.organomet.2c00095
Estat de la publicació	Publicada - 29 d’abr. 2022

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10.1021/acs.organomet.2c00095

https://ddd.uab.cat/record/293099

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CCDC 2111408: Experimental Crystal Structure Determination
Muñoz-Molina, J. M. (Creador), Bafaluy, D. (Col·laborador), Funes-Ardoiz, I. (Col·laborador), De Aguirre, A. (Col·laborador), Maseras, F. (Col·laborador), Belderrain, T. R. (Col·laborador), Pérez, P. J. (Col·laborador) & Muñiz, K. (Col·laborador), Cambridge Crystallographic Data Centre, 23 de set. 2021
DOI: 10.5517/ccdc.csd.cc28w2y6, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc28w2y6&sid=DataCite
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@article{c407878bdf0a45faabaacee746c032d5,

title = "Mechanistic Studies on the Synthesis of Pyrrolidines and Piperidines via Copper-Catalyzed Intramolecular C-H Amination",

abstract = "We have recently developed a method for the synthesis of pyrrolidines and piperidines via intramolecular C-H amination of N-fluoride amides using [TpxCuL] complexes as precatalysts [Tpx = tris(pyrazolyl)borate ligand and L = THF or CH3CN]. Herein, we report mechanistic studies on this transformation, which includes the isolation and structural characterization of a fluorinated copper(II) complex, [(TpiPr2OH)CuF] [TpiPr = hydrotris(3,5-diisopropylpyrazolyl)borate], pertinent to the mechanistic pathway. The effects of the nature of the Tpx ligand in the copper catalyst as well as of the halide in the N-X amides employed as reactants have been investigated both from experimental and computational perspectives.",

author = "Mu{\~n}oz-Molina, \{Jos{\'e} Mar{\'i}a\} and Daniel Bafaluy and Ignacio Funes-Ardoiz and \{De Aguirre\}, Adiran and Feliu Maseras and Belderrain, \{Tom{\'a}s R.\} and P{\'e}rez, \{Pedro J.\} and Kilian Mu{\~n}iz",

note = "Publisher Copyright: {\textcopyright} 2022 The Authors. Published by American Chemical Society.",

year = "2022",

month = apr,

day = "29",

doi = "10.1021/acs.organomet.2c00095",

language = "English",

volume = "41",

pages = "1099--1105",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "9",

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TY - JOUR

T1 - Mechanistic Studies on the Synthesis of Pyrrolidines and Piperidines via Copper-Catalyzed Intramolecular C-H Amination

AU - Muñoz-Molina, José María

AU - Bafaluy, Daniel

AU - Funes-Ardoiz, Ignacio

AU - De Aguirre, Adiran

AU - Maseras, Feliu

AU - Belderrain, Tomás R.

AU - Pérez, Pedro J.

AU - Muñiz, Kilian

PY - 2022/4/29

Y1 - 2022/4/29

N2 - We have recently developed a method for the synthesis of pyrrolidines and piperidines via intramolecular C-H amination of N-fluoride amides using [TpxCuL] complexes as precatalysts [Tpx = tris(pyrazolyl)borate ligand and L = THF or CH3CN]. Herein, we report mechanistic studies on this transformation, which includes the isolation and structural characterization of a fluorinated copper(II) complex, [(TpiPr2OH)CuF] [TpiPr = hydrotris(3,5-diisopropylpyrazolyl)borate], pertinent to the mechanistic pathway. The effects of the nature of the Tpx ligand in the copper catalyst as well as of the halide in the N-X amides employed as reactants have been investigated both from experimental and computational perspectives.

AB - We have recently developed a method for the synthesis of pyrrolidines and piperidines via intramolecular C-H amination of N-fluoride amides using [TpxCuL] complexes as precatalysts [Tpx = tris(pyrazolyl)borate ligand and L = THF or CH3CN]. Herein, we report mechanistic studies on this transformation, which includes the isolation and structural characterization of a fluorinated copper(II) complex, [(TpiPr2OH)CuF] [TpiPr = hydrotris(3,5-diisopropylpyrazolyl)borate], pertinent to the mechanistic pathway. The effects of the nature of the Tpx ligand in the copper catalyst as well as of the halide in the N-X amides employed as reactants have been investigated both from experimental and computational perspectives.

UR - https://www.scopus.com/pages/publications/85129957556

UR - https://www.mendeley.com/catalogue/1221340b-ce64-3baa-8b2c-e9036fc80f4b/

U2 - 10.1021/acs.organomet.2c00095

DO - 10.1021/acs.organomet.2c00095

M3 - Article

C2 - 35572769

AN - SCOPUS:85129957556

SN - 0276-7333

VL - 41

SP - 1099

EP - 1105

JO - Organometallics

JF - Organometallics

IS - 9

ER -

Mechanistic Studies on the Synthesis of Pyrrolidines and Piperidines via Copper-Catalyzed Intramolecular C-H Amination

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CCDC 2111408: Experimental Crystal Structure Determination

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