The Mizoroki–Heck Reaction Initiated Formal C(sp3)-H Arylation of Carbonyl Compounds

2021 ◽  
Author(s):  
Nan-Quan Jiang ◽  
Hai-Yan Li ◽  
Zhong-Jian Cai ◽  
Shun-Jun Ji
Keyword(s):  
Heck Reaction ◽  
Carbonyl Compounds ◽  
Reaction Proceeds

Herein, we present a Mizoroki–Heck reaction initiated formal C(sp3)-H arylation of α-methylcinnamaldehydes. The reaction proceeds smoothly under phosphane-free conditions, and provides a facile method to access important α-methylcinnamaldehyde derivatives with...

Aliphatic Radical Relay Heck Reaction at Unactivated C(sp3)–H Sites of Alcohols

2018 ◽  
Author(s):  
Padon Chuentragool ◽  
Dongari Yadagiri ◽  
Taiki Morita ◽  
Sumon Sarkar ◽  
Marvin Parasram ◽  
...  
Keyword(s):  
Visible Light ◽  
Heck Reaction ◽  
Room Temperature ◽  
Halogen Atom ◽  
Organic Molecules ◽  
Alkyl Halides ◽  
Aliphatic Alcohols ◽  
Aliphatic Radical ◽  
Reaction Proceeds

<div>The Mizoroki−Heck reaction is one of the most efficient methods for alkenylation of</div><div>aryl, vinyl, and alkyl halides. Due to its innate nature, this protocol requires the employment of compounds possessing a halogen atom at the site of functionalization. However, the accessibility of organic molecules possessing a halogen atom at a particular site in aliphatic systems is extremely limited. Thus, a protocol that would allow a Heck reaction to occur at a specific non-functionalized C(sp3)−H site would be highly desirable.</div><div>Here, we report a radical relay Heck reaction which allows for a selective remote</div>alkenylation of aliphatic alcohols at unactivated β-, γ- and δ-C(sp3 20 )–H sites. The use of easily installable/removable Si-based auxiliary enables selective I-atom/radical translocation events at remote C−H sites followed by the Heck reaction. Notably, the reaction proceeds smoothly under mild visible light-mediated conditions at room temperature, producing highly modifiable and valuable alkenol products from readily available alcohols feedstocks. <br>

Organometallic reactions in aqueous media — Antimony-mediated allylation of carbonyl compounds and the nature of allylstibine intermediates

2001 ◽  
Vol 79 (11) ◽  
pp. 1536-1540
Author(s):  
Lian-Hai Li ◽  
Tak Hang Chan
Keyword(s):  
Carbonyl Compounds ◽  
Good Yield ◽  
Allyl Bromide ◽  
Aqueous Media ◽  
Organometallic Reactions ◽  
Homoallylic Alcohols ◽  
Reaction Proceeds

Commercial antimony metal, in aqueous 1 M H(D)Cl solution, reacts with allyl bromide and aldehydes to give the corresponding homoallylic alcohols in good yield. The reaction proceeds through the formation of allylstibine intermediates. The structures of the allylstibine intermediates are likely to be allylstibine dibromide and diallylstibine bromide.Key words: allylation reaction, aqueous organometallic reactions, homoallylic alcohols, allylstibine dibromide, diallylstibine bromide.

Studying the reactivity of N-2-(2-aminobenzoyl)-N-phenyl-hydrazinecarbothioamide toward some selected carbonyl compounds

2018 ◽  
Vol 73 (6) ◽  
pp. 399-406 ◽  
Author(s):  
Asmaa H. Mohamed
Keyword(s):  
Spectral Data ◽  
Electron Donor ◽  
Carbonyl Compounds ◽  
Acceptor Interaction ◽  
Reaction Proceeds ◽  
Mechanisms Of Formation ◽  
Donor Acceptor

AbstractThe reactivity of N-2-(2-aminobenzoyl)-N-phenylhydrazinecarbothioamide (1) as an electron donor toward several electron-accepting compounds through electron donor-acceptor interaction has been studied. Thus, upon treatment of 1 with either 1,4-naphthoquinone, 2-dicyanomethyleneindan-1,3-dione, or 2,3-dichloro-1,4-naphthoquinone, the reaction proceeds to give thiadiazino[5,4-b]quinazoline, N-phenylcarbamohydrazonothioate, and thiadiazine-5,10-dione, respectively. Also, the reactivity of compound 1 toward some aldehydes and anhydrides was studied. The products were fully characterized by their spectral data. The mechanisms of formation of the products have been rationalized.

Investigation of the reactivity of 4-amino-5-hydrazineyl-4H-1,2, 4-triazole-3-thiol towards some selected carbonyl compounds: synthesis of novel triazolotriazine-, triazolotetrazine-, and triazolopthalazine derivatives

2019 ◽  
Vol 74 (11-12) ◽  
pp. 847-855
Author(s):  
Kamal M. El-Shaieb ◽  
Asmaa H. Mohamed ◽  
Fathy F. Abdel-latif
Keyword(s):  
Mass Spectrometry ◽  
Elemental Analysis ◽  
Carbonyl Compounds ◽  
Spectroscopic Data ◽  
Pyromellitic Dianhydride ◽  
Isatoic Anhydride ◽  
Naphthalic Anhydride ◽  
H Nmr ◽  
Reaction Proceeds ◽  
C Nmr

AbstractThe reactivity of 4-amino-5-hydrazineyl-4H-1,2,4-triazole-3-thiol (1) towards several carbonyl compounds was investigated. We have found that on treatment of 1 with isatoic anhydride (2), 1,8-naphthalic anhydride (4), diphenic anhydride (6), pyromellitic dianhydride (8), and tetrabromophthalic anhydride (10), the reaction proceeds to give triazolotetrazine- and triazolophthalazine derivatives in good yields using simple experimental procedures. The structure of the synthesized compounds was confirmed using different spectroscopic data (1H NMR, 13C NMR, mass spectrometry, and elemental analysis). The mechanism of the obtained products was also discussed.

Palladium-Catalyzed Heck Reaction on 1-Alkoxy-1,3-dienes:  A Regioselective γ-Arylation of α,β-Unsaturated Carbonyl Compounds

2003 ◽  
Vol 5 (21) ◽  
pp. 3815-3817 ◽  
Author(s):  
Annamaria Deagostino ◽  
Cristina Prandi ◽  
Paolo Venturello
Keyword(s):  
Heck Reaction ◽  
Carbonyl Compounds ◽  
Palladium Catalyzed

Geminal bis(silane)-controlled regio- and stereoselective oxidative Heck reaction of enol ethers with terminal alkenes to give push–pull 1,3-dienes

2015 ◽  
Vol 51 (85) ◽  
pp. 15546-15549 ◽  
Author(s):  
Linjie Li ◽  
Yang Chu ◽  
Lu Gao ◽  
Zhenlei Song
Keyword(s):  
Heck Reaction ◽  
Enol Ethers ◽  
Reaction Proceeds ◽  
Terminal Alkenes

A geminal bis(silane)-controlled regio- and stereoselective oxidative Heck reaction of enol ethers with terminal alkenes has been developed. The reaction proceeds with α,β-coupling regioselectivity to give push–pull Z,E-1,3-dienes in good yields.

Aliphatic Radical Relay Heck Reaction at Unactivated C(sp3)–H Sites of Alcohols

2018 ◽  
Author(s):  
Padon Chuentragool ◽  
Dongari Yadagiri ◽  
Taiki Morita ◽  
Sumon Sarkar ◽  
Marvin Parasram ◽  
...  
Keyword(s):  
Visible Light ◽  
Heck Reaction ◽  
Room Temperature ◽  
Halogen Atom ◽  
Organic Molecules ◽  
Alkyl Halides ◽  
Aliphatic Alcohols ◽  
Aliphatic Radical ◽  
Reaction Proceeds

<div>The Mizoroki−Heck reaction is one of the most efficient methods for alkenylation of</div><div>aryl, vinyl, and alkyl halides. Due to its innate nature, this protocol requires the employment of compounds possessing a halogen atom at the site of functionalization. However, the accessibility of organic molecules possessing a halogen atom at a particular site in aliphatic systems is extremely limited. Thus, a protocol that would allow a Heck reaction to occur at a specific non-functionalized C(sp3)−H site would be highly desirable.</div><div>Here, we report a radical relay Heck reaction which allows for a selective remote</div>alkenylation of aliphatic alcohols at unactivated β-, γ- and δ-C(sp3 20 )–H sites. The use of easily installable/removable Si-based auxiliary enables selective I-atom/radical translocation events at remote C−H sites followed by the Heck reaction. Notably, the reaction proceeds smoothly under mild visible light-mediated conditions at room temperature, producing highly modifiable and valuable alkenol products from readily available alcohols feedstocks. <br>

Palladium-catalyzed δ-selective reductive Heck reaction of alkenyl carbonyl compounds with aryl iodides and bromides

2020 ◽  
Vol 7 (16) ◽  
pp. 2216-2223 ◽  
Author(s):  
Yang Li ◽  
Jun-Fang Gong ◽  
Mao-Ping Song
Keyword(s):  
Heck Reaction ◽  
Carbonyl Compounds ◽  
Pentanoic Acid ◽  
Aryl Iodides ◽  
Palladium Catalyzed

A simple, operationally convenient and highly regioselective palladium-catalyzed reductive Heck reaction of alkenyl carbonyl compounds with aryl iodides and bromides has been developed to afford structurally diverse δ-aryl pentanoic acid derivatives.

Observations of the Thermal Decomposition of Brucite

1968 ◽  
Vol 26 ◽  
pp. 446-447
Author(s):  
P. L. Burnett ◽  
W. R. Mitchell ◽  
C. L. Houck
Keyword(s):  
Thermal Decomposition ◽  
Magnesium Oxide ◽  
Basal Plane ◽  
Magnesium Ions ◽  
A Value ◽  
Reaction Proceeds

Natural Brucite (Mg(OH)2) decomposes on heating to form magnesium oxide (MgO) having its cubic ﹛110﹜ and ﹛111﹜ planes respectively parallel to the prism and basal planes of the hexagonal brucite lattice. Although the crystal-lographic relation between the parent brucite crystal and the resulting mag-nesium oxide crystallites is well known, the exact mechanism by which the reaction proceeds is still a matter of controversy. Goodman described the decomposition as an initial shrinkage in the brucite basal plane allowing magnesium ions to shift their original sites to the required magnesium oxide positions followed by a collapse of the planes along the original <0001> direction of the brucite crystal. He noted that the (110) diffraction spots of brucite immediately shifted to the positions required for the (220) reflections of magnesium oxide. Gordon observed separate diffraction spots for the (110) brucite and (220) magnesium oxide planes. The positions of the (110) and (100) brucite never changed but only diminished in intensity while the (220) planes of magnesium shifted from a value larger than the listed ASTM d spacing to the predicted value as the decomposition progressed.

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