Synthesis of Difluoroglycine Derivatives from Amines, Difluorocarbene, and CO <subscript>2</subscript> : Computational Design, Scope, and Applications. - OpacWWW

Tytuł:: Synthesis of Difluoroglycine Derivatives from Amines, Difluorocarbene, and CO 2 : Computational Design, Scope, and Applications.
Autorzy:: Hayashi H; Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, Hokkaido, 0010021, Japan.; JST, ERATO Maeda Artificial Intelligence in Chemical Reaction, Design and Discovery Project, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido, 0600810, Japan.
Takano H; Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, Hokkaido, 0010021, Japan.; JST, ERATO Maeda Artificial Intelligence in Chemical Reaction, Design and Discovery Project, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido, 0600810, Japan.
Katsuyama H; Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, Hokkaido, 0010021, Japan.; JST, ERATO Maeda Artificial Intelligence in Chemical Reaction, Design and Discovery Project, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido, 0600810, Japan.
Harabuchi Y; Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, Hokkaido, 0010021, Japan.; JST, ERATO Maeda Artificial Intelligence in Chemical Reaction, Design and Discovery Project, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido, 0600810, Japan.; Department of Chemistry, Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido, 0600810, Japan.
Maeda S; Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, Hokkaido, 0010021, Japan.; JST, ERATO Maeda Artificial Intelligence in Chemical Reaction, Design and Discovery Project, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido, 0600810, Japan.; Department of Chemistry, Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido, 0600810, Japan.; Research and Services Division of Materials Data and Integrated System (MaDIS), National Institute for Materials Science (NIMS), Tsukuba, Ibaraki, 3050044, Japan.
Mita T; Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, Hokkaido, 0010021, Japan.; JST, ERATO Maeda Artificial Intelligence in Chemical Reaction, Design and Discovery Project, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido, 0600810, Japan.
Źródło:: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2021 Jul 12; Vol. 27 (39), pp. 10040-10047. Date of Electronic Publication: 2021 May 28.
Typ publikacji:: Journal Article
Język:: English
Imprint Name(s):: Original Publication: Weinheim, Germany : Wiley-VCH
MeSH Terms:: Amines*
Carbon Dioxide*
Hydrocarbons, Fluorinated
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Grant Information:: JPMJER1903 Exploratory Research for Advanced Technology; 18K05096 Japan Society for the Promotion of Science; Sumitomo Foundation; Astellas Foundation for Research on Metabolic Disorders; Akiyama Life Science Foundation; Ube Foundation; Fugaku Trust for Medicinal Research; Uehara Memorial Foundation
Contributed Indexing:: Keywords: carbon dioxide fixation; difluorocarbene; difluoroglycine; fluorination; multicomponent reactions
Substance Nomenclature:: 0 (Amines)
0 (Hydrocarbons, Fluorinated)
0 (difluorocarbene)
142M471B3J (Carbon Dioxide)
Entry Date(s):: Date Created: 20210430 Date Completed: 20210715 Latest Revision: 20210715
Update Code:: 20240104
DOI:: 10.1002/chem.202100812
PMID:: 33929060
: Czasopismo naukowe

Pełny tekst

A three-component reaction (3CR) for the synthesis of difluoroglycine derivatives has been achieved by using amines, difluorocarbene (generated in situ), and the abundant, inexpensive, and nontoxic C 1 source CO 2 . Various tert-amines and pyridine, (iso)quinoline, imidazole, thiazole, and pyrazole derivatives were incorporated, and the corresponding products were isolated in solid form without purification by column chromatography on silica gel. Detailed reaction profiles of the 3CR were obtained from computational analysis using DFT calculations, and the results critically suggest that simple ammonia is not applicable to this reaction. In addition, as strongly supported by computational predictions, a new reagent that can generate difluorocarbene at 0 °C without any additives was discovered. Finally, radical substitution reactions of the obtained difluoroglycine derivatives under photoredox conditions, as well as a synthetic application as an N-heterocyclic carbene ligand are shown.
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Synthesis of Difluoroglycine Derivatives from Amines, Difluorocarbene, and CO 2 : Computational Design, Scope, and Applications.