Aminomethylation of Functionalized Organozinc Reagents and Grignard Reagents Using Immonium Trifluoroacetates

Synthesis ◽  
2000 ◽  
Vol 2000 (07) ◽  
pp. 941-948 ◽  
Author(s):  
Nicolas Millot ◽  
Claudia Piazza ◽  
Salvatore Avolio ◽  
Paul Knochel
Keyword(s):  
Grignard Reagents ◽  
Organozinc Reagents

Synthesis of allyl-aziridines from α-halo oxime ethers and allyl zinc bromides

RSC Advances ◽  
2016 ◽  
Vol 6 (31) ◽  
pp. 26437-26440 ◽  
Author(s):  
Songlin Zheng ◽  
Songlin Zhang
Keyword(s):  
Grignard Reagents ◽  
Mild Conditions ◽  
Novel Method ◽  
Organozinc Reagents

A novel method for the preparation of allyl aziridines by reacting α-halo oxime ethers with allylic zinc reagents under mild conditions. Some advantages of using organozinc reagents are that they are easily prepared, non-toxic, and more selective than Grignard reagents.

Recent Advances in the Synthesis of Enantiomerically Enriched Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols through Addition of Organometallic Reagents to Carbonyl Compounds

Synthesis ◽  
2020 ◽  
Vol 52 (13) ◽  
pp. 1855-1873
Author(s):  
Senthil Narayanaperumal ◽  
Ricardo S. Schwab ◽  
Wystan K. O. Teixeira ◽  
Danilo Yano de Albuquerque
Keyword(s):  
Carbonyl Compounds ◽  
Building Blocks ◽  
Short Review ◽  
Biological Properties ◽  
Enantioselective Synthesis ◽  
Grignard Reagents ◽  
Organometallic Reagents ◽  
Important Family ◽  
Organolithium Reagents ◽  
Organozinc Reagents

Enantiomerically enriched diaryl, aryl heteroaryl, and dihetero­aryl alcohols are an important family of compounds known for their biological properties. Moreover, these molecules are highly privileged scaffolds used as building blocks for the synthesis of pharmaceutically relevant products. This short review provides background on the enantioselective arylation and heteroarylation of carbonyl compounds, as well as, the most significant improvements in this field with special emphasis on the application of organometallic reagents.1 Introduction2 Background on the Enantioselective Synthesis of Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols3 Organozinc Reagents4 Organolithium Reagents5 Grignard Reagents6 Organoaluminum Reagents7 Organotitanium Reagents8 Organobismuth Reagents9 Miscellaneous10 Conclusion

Catalytic enantioselective alkyl and aryl addition to aldehydes and ketones with organozinc reagents derived from alkyl Grignard reagents or arylboronic acids

2011 ◽  
Vol 1 (7) ◽  
pp. 1149 ◽  
Author(s):  
Manabu Hatano ◽  
Riku Gouzu ◽  
Tomokazu Mizuno ◽  
Hitoshi Abe ◽  
Toshihide Yamada ◽  
...  
Keyword(s):  
Grignard Reagents ◽  
Arylboronic Acids ◽  
Aldehydes And Ketones ◽  
Organozinc Reagents

ChemInform Abstract: Aminomethylation of Functionalized Organozinc Reagents and Grignard Reagents Using Immonium Trifluoroacetates.

ChemInform ◽  
2000 ◽  
Vol 31 (41) ◽  
pp. no-no
Author(s):  
Nicolas Millot ◽  
Claudia Piazza ◽  
Salvatore Avolio ◽  
Paul Knochel
Keyword(s):  
Grignard Reagents ◽  
Organozinc Reagents

Fe-Catalyzed Conjunctive Cross-Couplings of Unactivated Alkenes with Grignard Reagents

2020 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Cassandra R. Youshaw ◽  
Mingbin Yuan ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Functional Groups ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Turnover Frequency ◽  
Diverse Range ◽  
Cascade Cyclization ◽  
Radical Cascade

The first iron-catalyzed three-component cross-coupling of unactivated olefins with alkyl halides and Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp2-hybridized nucleophiles, alkyl halides, and unactivated olefins bearing diverse functional groups to yield the desired 1,2-alkylarylated products with high regiocontrol. Further, we demonstrate that this protocol is amenable for the synthesis of new (hetero)carbocycles including tetrahydrofurans and pyrrolidines via a three-component radical cascade cyclization/arylation that forges three new C-C bonds.

Design and Development of Fe-Catalyzed Intra- and Intermolecular Carbofunctionalization of Vinyl Cyclopropanes

2019 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Mingbin Yuan ◽  
Chris Acha ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Mechanistic Studies ◽  
Radical Intermediates ◽  
Design And Implementation ◽  
Solvent Cage ◽  
Radical Cascade ◽  
Radical Processes

Design and implementation of the first (asymmetric) Fe-catalyzed intra- and intermolecular difunctionalization of vinyl cyclopropanes (VCPs) with alkyl halides and aryl Grignard reagents has been realized via a mechanistically driven approach. Mechanistic studies support the diffusion of the alkyl radical intermediates out of the solvent cage to participate in an intra- or -intermolecular radical cascade with the VCP followed by re-entering the Fe radical cross-coupling cycle to undergo selective C(sp2)-C(sp3) bond formation. Overall, we provide new design principles for Fe-mediated radical processes and underscore the potential of using combined computations and experiments to accelerate the development of challenging transformations.

Alkyl 1-[2-(oxido anion)-, 3-, 4-, 5-alkyl substituted]phenyl ketyl radicals

1979 ◽  
Vol 44 (6) ◽  
pp. 1731-1741 ◽  
Author(s):  
Andrej Staško ◽  
Ľubomír Malík ◽  
Alexander Tkáč ◽  
Vladimír Adamčík ◽  
Eva Maťašová
Keyword(s):  
Electron Donor ◽  
Unpaired Electron ◽  
Grignard Reagents ◽  
Slight Effect ◽  
Benzene Nucleus ◽  
Alkyl Groups ◽  
Splitting Constant

Reactions of R2,R3-alkyl substituted 2-hydroxybenzenecarboxylic acids 2-HO-C6H2R2-COOH with Grignard reagents R1MgBr in the presence of nickel give stable aryl alkyl ketyl radicals 2-O--R2-, R3-C6H2-CO--R1 where R1 = CH3, C2H5, C2D5, n-C3H7 and R2,R3 = CH3, C2H5, i-C3H7, t-C4H9. The β protons of ketyl group are equivalent (splitting constant 1.25 mT) and non-equivalent (splitting constants within 0.5 to 1.5 mT) for R1 = methyl and other alkyl groups, respectively. Interaction of the γ protons with the unpaired electron was only observed in the case of R1 = n-propyl (splitting constants about 0.07 mT). The substituents R1 have but slight effect on values of splitting constants of the protons in R2,R3 and vice versa. Also splitting constants of the benzene nucleus (a4H = 0.55 mT, a6H = 0.44 mT) are only slightly affected by the substituents R1,R2,R3, which indicates dominant electron-donor effect of the oxido-anion group eliminating the relatively smaller contributions of the alkyl substituents.

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