Iron-catalyzed cross coupling of P–H/C–O bonds: efficient synthesis of α-alkoxyphosphorus compounds

2016 ◽  
Vol 45 (5) ◽  
pp. 1877-1880 ◽  
Author(s):  
Xue Li ◽  
Tieqiao Chen ◽  
Yuta Saga ◽  
Li-Biao Han
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Efficient Synthesis ◽  
Mild Conditions ◽  
Reaction Proceeds ◽  
First Time

An efficient P–C bond-formation through iron-catalyzed cross coupling of P–H/C–O bonds is developed for the first time. This reaction proceeds efficiently to produce the corresponding valuable α-alkoxyphosphorus compounds under mild conditions with a wide generality.

scholarly journals Nickel-Catalyzed Asymmetric Reductive Cross-Coupling of α-Chloroesters with (Hetero)Aryl Iodides

2021 ◽  
Author(s):  
Travis DeLano ◽  
Sara Dibrell ◽  
Caitlin R. Lacker ◽  
Adam Pancoast ◽  
Kelsey Poremba ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Mild Conditions ◽  
Aryl Iodides ◽  
Reaction Proceeds

An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities....

Neodymium-Promoted Highly Selective Carbon–Carbon Double Bond Formation of Ketones with Allyl Halides in the Presence of Diethyl Phosphite

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3446-3451
Author(s):  
Songlin Zhang ◽  
Dengbing Xie ◽  
Yiqiong Wang ◽  
Bo Yang
Keyword(s):  
Double Bond ◽  
Bond Formation ◽  
Point Of View ◽  
Diethyl Phosphite ◽  
Reaction Conditions ◽  
One Pot ◽  
Mild Conditions ◽  
Carbon Double Bond ◽  
Allyl Halides ◽  
First Time

The carbon–carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly α-regioselective and was conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with feasible reaction conditions.

7,10-Dibromo-2,3-dicyanopyrazinophenanthrene Aggregates as a Photosensitizer for Nickel-Catalyzed Aryl Esterification

Synlett ◽  
2021 ◽  
Author(s):  
Xiaoqiang Yu ◽  
Min He ◽  
Shilei Yang ◽  
Ming Bao
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Bond Formation ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Ni Catalyst ◽  
Coupling Reactions ◽  
Formation Reaction ◽  
Cross Coupling Reactions ◽  
Reaction Proceeds

AbstractSelf-assembled aggregates of 7,10-dibromo-2,3-dicyanopyrazinophenanthrene which act as a new organophotocatalyst in combination with Ni catalyst for the Caryl–Oacyl cross-coupling reactions of carboxylic acids with aryl halides are described. This visible-light-induced Caryl–Oacyl bond-formation reaction proceeds smoothly to afford aryl esters with satisfactory to excellent yields.

scholarly journals Palladium-Catalyzed Cross-Coupling of Gem-Bromofluoroalkenes with Alkylboronic Acids for the Synthesis of Alkylated Monofluoroalkenes

Molecules ◽  
2020 ◽  
Vol 25 (23) ◽  
pp. 5532
Author(s):  
Laëtitia Chausset-Boissarie ◽  
Nicolas Cheval ◽  
Christian Rolando
Keyword(s):  
Organic Synthesis ◽  
Functional Group ◽  
Materials Science ◽  
Cross Coupling ◽  
High Yield ◽  
Efficient Synthesis ◽  
Mild Conditions ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Novel Strategy

Monofluoroalkenes are versatile fluorinated synthons in organic synthesis, medicinal chemistry and materials science. In light of the importance of alkyl-substituted monofluoroalkenes efficient synthesis of these moieties still represents a synthetic challenge. Herein, we described a mild and efficient methodology to obtain monofluoroalkenes through a stereospecific palladium-catalyzed alkylation of gem-bromofluoroalkenes with primary and strained secondary alkylboronic acids under mild conditions. This novel strategy gives access to a wide range of functionalized tri- and tetrasubstituted monofluoroalkenes in high yield, with good functional group tolerance, independently from the gem-bromofluoroalkenes geometry.

scholarly journals C–C Bond formation catalyzed by natural gelatin and collagen proteins

2013 ◽  
Vol 9 ◽  
pp. 1111-1118 ◽  
Author(s):  
Dennis Kühbeck ◽  
Basab Bijayi Dhar ◽  
Eva-Maria Schön ◽  
Carlos Cativiela ◽  
Vicente Gotor-Fernández ◽  
...  
Keyword(s):  
Bond Formation ◽  
Scale Up ◽  
Product Yield ◽  
Order Rate Constant ◽  
Physiological Conditions ◽  
First Order ◽  
Bond Forming ◽  
Mild Conditions ◽  
Nitroaldol Reaction ◽  
First Time

The activity of gelatin and collagen proteins towards C–C bond formation via Henry (nitroaldol) reaction between aldehydes and nitroalkanes is demonstrated for the first time. Among other variables, protein source, physical state and chemical modification influence product yield and kinetics, affording the nitroaldol products in both aqueous and organic media under mild conditions. Significantly, the scale-up of the process between 4-nitrobenzaldehyde and nitromethane is successfully achieved at 1 g scale and in good yield. A comparative kinetic study with other biocatalysts shows an increase of the first-order rate constant in the order chitosan < gelatin < bovine serum albumin (BSA) < collagen. The results of this study indicate that simple edible gelatin can promote C–C bond forming reactions under physiological conditions, which may have important implications from a metabolic perspective.

A Photoredox-Catalyzed Four Component Reaction for the Atom-Efficient Synthesis of Complex Secondary Amines

2020 ◽  
Author(s):  
Lisa Marie Kammer ◽  
Matthias Krumb ◽  
Benjamin Spitzbarth ◽  
Benjamin Lipp ◽  
Jonas Kühlborn ◽  
...  
Keyword(s):  
Secondary Amines ◽  
Efficient Synthesis ◽  
One Pot ◽  
Simultaneous Formation ◽  
Mild Conditions ◽  
Simple Protocol ◽  
Reaction Proceeds ◽  
Styrene Derivatives ◽  
The One ◽  
Single Bonds

The one-pot sulfonylation/aminoalkylation of styrene derivatives furnishing highly substituted gamma-sulfonylamines was accomplished through a photoredox-catalyzed four-component reaction. Apart from one molecule of water and the sodium counterion of the sulfinate, all atoms of the starting materials are transferred to the final product, rendering this process highly atom-efficient. The operationally simple protocol allows for the simultaneous formation of three new single bonds (C–S, C–N, and C–C) and therefore grants rapid access to structurally diverse products. The reaction proceeds under mild conditions in aqueous acetonitrile and shows a broad scope, including natural products and drug-like molecules.

A Photoredox-Catalyzed Four Component Reaction for the Atom-Efficient Synthesis of Complex Secondary Amines

2020 ◽  
Author(s):  
Lisa Marie Kammer ◽  
Matthias Krumb ◽  
Benjamin Spitzbarth ◽  
Benjamin Lipp ◽  
Jonas Kühlborn ◽  
...  
Keyword(s):  
Secondary Amines ◽  
Efficient Synthesis ◽  
One Pot ◽  
Simultaneous Formation ◽  
Mild Conditions ◽  
Simple Protocol ◽  
Reaction Proceeds ◽  
Styrene Derivatives ◽  
The One ◽  
Single Bonds

The one-pot sulfonylation/aminoalkylation of styrene derivatives furnishing highly substituted gamma-sulfonylamines was accomplished through a photoredox-catalyzed four-component reaction. Apart from one molecule of water and the sodium counterion of the sulfinate, all atoms of the starting materials are transferred to the final product, rendering this process highly atom-efficient. The operationally simple protocol allows for the simultaneous formation of three new single bonds (C–S, C–N, and C–C) and therefore grants rapid access to structurally diverse products. The reaction proceeds under mild conditions in aqueous acetonitrile and shows a broad scope, including natural products and drug-like molecules.

Cu(II)/vasicine promoted intramolecular C-O formation: synthesis of benzoxazoles in EtOH

2020 ◽  
Vol 17 ◽  
Author(s):  
Minxin Li ◽  
Meiling Li ◽  
Yanling Tang ◽  
Yun Sun ◽  
Lu Qu ◽  
...  
Keyword(s):  
Catalytic System ◽  
Aromatic Compounds ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
High Yields

Aim and Objective: Benzoxazoles are valuable bicyclic aromatic compounds, the construction of benzoxazoles via C-O cross-coupling reactions has attracted more and more attention. Materials and Methods: The best condition of C-O bond formation from o-haloanilides was carried out taking Cu(OTf)2 (5 mol%) and vasicine (10 mol%) as the catalyst in EtOH in present of K2CO3 (2 eq.) for 12 h at 90oC. Results: A series of 2-substituted benzoxazoles have been prepared in high yields from 2-bromoanilides and 2-iodioanilides under mild conditions. Conclusion: We have developed an efficient Cu-vasicine catalytic system for intramolecular C-O bond formation. This strategy is applicable to synthesis of a wide variety of 2-substituted benzoxazoles by intramolecular O-arylation of o-haloanilides.

Enantioselective Reductive Diarylation of Alkenes by Ni-Catalyzed Domino Heck Cyclization/Cross Coupling

Synlett ◽  
2019 ◽  
Vol 30 (09) ◽  
pp. 1008-1014 ◽  
Author(s):  
Kuai Wang ◽  
Wangqing Kong
Keyword(s):  
Functional Groups ◽  
High Efficiency ◽  
Cross Coupling ◽  
Quaternary Centers ◽  
Mild Conditions ◽  
Rapid Access ◽  
Heck Cyclization ◽  
Aryl Bromides ◽  
First Time ◽  
Very High

A Ni-catalyzed enantioselective reductive diarylation of alkenes through a tandem Heck cyclization/cross coupling of two structurally distinguished aryl bromides is accomplished for the first time. This reaction takes place under very mild conditions with high efficiency and tolerates a variety of functional groups. Thus, it provides a rapid access to various medicinally relevant bis-heterocycles containing all-carbon quaternary centers with very high enantioselectivity.

scholarly journals Atroposelective antibodies as a designed protein scaffold for artificial metalloenzymes

2019 ◽  
Vol 9 (1) ◽  
Author(s):  
Takuma Adachi ◽  
Akira Harada ◽  
Hiroyasu Yamaguchi
Keyword(s):  
Bond Formation ◽  
Metal Catalysts ◽  
Alkylation Reaction ◽  
Protein Scaffold ◽  
Asymmetric Catalysts ◽  
Reaction Proceeds ◽  
Cu Catalyst ◽  
Artificial Metalloenzymes ◽  
First Time ◽  
Protein Environment

Abstract Design and engineering of protein scaffolds are crucial to create artificial metalloenzymes. Herein we report the first example of C-C bond formation catalyzed by artificial metalloenzymes, which consist of monoclonal antibodies (mAbs) and C2 symmetric metal catalysts. Prepared as a tailored protein scaffold for a binaphthyl derivative (BN), mAbs bind metal catalysts bearing a 1,1′-bi-isoquinoline (BIQ) ligand to yield artificial metalloenzymes. These artificial metalloenzymes catalyze the Friedel-Crafts alkylation reaction. In the presence of mAb R44E1, the reaction proceeds with 88% ee. The reaction catalyzed by Cu-catalyst incorporated into the binding site of mAb R44E1 is found to show excellent enantioselectivity with 99% ee. The protein environment also enables the use of BIQ-based catalysts as asymmetric catalysts for the first time.

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