Dirhodium(ii)/P(t-Bu)3 catalyzed tandem reaction of α,β-unsaturated aldehydes with arylboronic acids

2018 ◽  
Vol 16 (40) ◽  
pp. 7470-7476 ◽  
Author(s):  
Ziling Ma ◽  
Yuanhua Wang
Keyword(s):  
Tandem Reaction ◽  
Arylboronic Acids ◽  
Unsaturated Aldehydes ◽  
High Yields

Axially alkylphosphane ligated Rh2(OAc)4 catalyzes the tandem reaction of α,β-unsaturated aldehydes with arylboronic acids to produce ketone derivatives in high yields.

Assembly of Fluorinated Chromanones via Enantioselective Tandem Reaction

2021 ◽  
Author(s):  
Mengxue Lu ◽  
Zongli Xiong ◽  
Yuqiao Zhou ◽  
Xin Wang ◽  
Xiaoyi Li ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Tandem Reaction ◽  
Unsaturated Aldehydes ◽  
Stereogenic Centers ◽  
First Time

The enantioselective synthesis of fluorinated tricyclic chromanones with multiple vicinal stereogenic centers has been realized for the first time, through the tandem reaction between 2-fluorinated 1-(2-hydroxyaryl)-1,3-diketones and α,β-unsaturated aldehydes. In...

Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Aldehydes Catalyzed by a Chiral Diene–Rhodium Complex

2005 ◽  
Vol 34 (11) ◽  
pp. 1480-1481 ◽  
Author(s):  
Tamio Hayashi ◽  
Norihito Tokunaga ◽  
Kazuhiro Okamoto ◽  
Ryo Shintani
Keyword(s):  
Rhodium Complex ◽  
Arylboronic Acids ◽  
Unsaturated Aldehydes

Mn(OAc)3 induced C-4 arylations of quinazoline 3-oxides with arylboronic acids

Synthesis ◽  
2021 ◽  
Author(s):  
Rashinikumar Samandram ◽  
Meliha Çetin Korukçu ◽  
Necdet Coskun
Keyword(s):  
Aromatic Rings ◽  
Arylboronic Acids ◽  
Manganese Triacetate ◽  
High Yields

The use of manganese triacetate as an oxidant component in the C-4 arylations of 2-aryl-quinazoline 3-oxides with arylboronic acids is reported. The new protocol was applied to prepare new 2,4-diarylated quinazoline 3-oxides in good to high yields. The method was shown to tolerate various substituents on both aromatic rings, and no complications as deoxygenation and rearrangement to quinazolin-4(3H)-one was observed.

TYLENOL® and ASPIRIN® as green promoters for ipso-hydroxylation of arylboronic acids

2021 ◽  
Vol 18 ◽  
Author(s):  
Gyu-Tae Kwon ◽  
Seung-Hoi Kim
Keyword(s):  
Phenolic Compound ◽  
Catalytic Amount ◽  
Aerobic Conditions ◽  
Arylboronic Acids ◽  
High Yields

: We explored the most expedient pathway for phenolic compound preparation using a combination of arylboronic acids, a green oxidant (H2O2) and a catalytic amount of readily available medicinal materials (TYLENOL® and ASPIRIN®). The ayrlboronic acids were successfully transformed into the corresponding phenols in high yields under metal- and base-free aqueous aerobic conditions. We demonstrated that enhanced availability and sustainability are some advantages associated with the use of medicinal supports.

Nickel-catalyzed carbodifunctionalization of N-vinylamides enables access to γ-amino acids

2020 ◽  
Vol 56 (17) ◽  
pp. 2642-2645 ◽  
Author(s):  
Zhi-Fang Yang ◽  
Chang Xu ◽  
Xing Zheng ◽  
Xingang Zhang
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Tandem Reaction ◽  
Amino Acid Esters ◽  
Arylboronic Acids ◽  
Acid Esters

A nickel-catalyzed tandem reaction of N-vinylamides with arylboronic acids and bromodifluoroacetate has been developed. The reaction efficiently furnishes a series of protected α,α-difluoro-γ-amino acid esters.

A Facile Microwave and SnCl2 Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

2020 ◽  
Vol 73 (12) ◽  
pp. 1176
Author(s):  
Nicholas S. O'Brien ◽  
Adam McCluskey
Keyword(s):  
Microwave Irradiation ◽  
Diels Alder ◽  
Electrophilic Addition ◽  
Pure Material ◽  
Robust Approach ◽  
Unsaturated Aldehydes ◽  
Biological Importance ◽  
High Yields ◽  
Aromatic Heterocyclic

An elegantly simple, facile, and robust approach to a scaffold of biological importance, 2,3-dihydroquinazolin-4(1H)-ones, is reported. A catalytic 1% SnCl2/microwave-mediated approach afforded access to pure material, collected by cooling and filtration after 20-min microwave irradiation at 120°C. A total of 41 analogues were prepared in isolated yields of 17–99%. This process was highly tolerant of aliphatic, aromatic, heterocyclic, and acyclic aldehydes, but furan, pyrrole, and thiophene aldehyde reactivity correlated with propensity towards electrophilic addition and/or Diels–Alder addition. As a result, thiophene afforded high yields (80%) whereas pyrrole carboxaldehyde failed to react. With simple cinnamaldehydes, and in the SbCl3-mediated reaction, and with α,β-unsaturated aldehydes the equivalent quinazolin-4(3H)-ones, and not the 2,3-dihydroquinazolin-4(1H)-ones, was favoured.

scholarly journals Regioselective synthesis of benzonitriles via amino-catalyzed [3+3] benzannulation reaction

2020 ◽  
Vol 44 (9-10) ◽  
pp. 592-597
Author(s):  
Lin Jiang ◽  
Wen-Fei Jin ◽  
Liu-Dong Yu ◽  
Ming-Wei Yuan ◽  
Hong-Li Li ◽  
...  
Keyword(s):  
Environmentally Friendly ◽  
Regioselective Synthesis ◽  
Reaction Conditions ◽  
Unsaturated Aldehydes ◽  
High Yields ◽  
Environmentally Friendly Method

A straightforward synthesis of benzonitriles is achieved via amino-catalyzed [3+3] benzannulation of α,β-unsaturated aldehydes and 4-arylsulfonyl-2-butenenitriles. Using pyrrolidine as an organocatalyst via iminium activation, a series of substituted benzonitriles were obtained in good to high yields in a regioselective manner. This reaction can proceed smoothly under mild reaction conditions and without the aid of any metals, additional oxidants, or strong bases, thus making this an efficient and environmentally friendly method to access benzonitriles.

One-pot atom-efficient synthesis of bio-renewable polyesters and cyclic carbonates through tandem catalysis

2015 ◽  
Vol 51 (40) ◽  
pp. 8504-8507 ◽  
Author(s):  
Fan Jia ◽  
Xiaoyu Chen ◽  
Yan Zheng ◽  
Yusheng Qin ◽  
Youhua Tao ◽  
...  
Keyword(s):  
Tandem Reaction ◽  
Cyclic Carbonates ◽  
Tandem Catalysis ◽  
Efficient Synthesis ◽  
One Pot ◽  
One Pot Synthesis ◽  
Salen Complexes ◽  
High Yields ◽  
First Time

One-pot synthesis of well-defined bio-renewable polyesters and cyclic carbonates in high yields was successfully realized for the first time by way of a tandem reaction using metal salen complexes as catalysts.

Cyanoethylations and Michael additions. II. The synthesis of allylic cyclohexenols by γ-cyanoethylation of α,β-unsaturated aldehydes and ketones. Part II

1970 ◽  
Vol 48 (18) ◽  
pp. 2819-2838 ◽  
Author(s):  
Ch. R. Engel ◽  
J. Lessard
Keyword(s):  
Membered Ring ◽  
Detailed Report ◽  
Michael Additions ◽  
Unsaturated Aldehydes ◽  
Single Operation ◽  
Aldehydes And Ketones ◽  
High Yields

The detailed report of the first cyclo-γ-cyanoethylation of an α,β-unsaturated carbonyl system, 3β-acetoxy-5α-pregn-17-en-21-al, is given. This reaction, which proceeds in high yields, gives rise, in a single operation, to products with an additional functionalized six-membered ring, primarily to allylic α′-cyanohexenols.

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