scholarly journals Fe-catalyzed esterification of amides via C–N bond activation

RSC Advances ◽  
2018 ◽  
Vol 8 (9) ◽  
pp. 4571-4576 ◽  
Author(s):  
Xiuling Chen ◽  
Siying Hu ◽  
Rongxing Chen ◽  
Jian Wang ◽  
Minghu Wu ◽  
...  
Keyword(s):  
Functional Group ◽  
Bond Activation ◽  
Environmentally Friendly ◽  
Tertiary Amides

An efficient Fe-catalyzed esterification of primary, secondary, and tertiary amides with various alcohols was performed. Esterification was accomplished with inexpensive, environmentally friendly FeCl3·6H2O, and with high functional group tolerance

scholarly journals Homocoupling of terminal alkynes catalyzed by CuCl under solvent-free conditions

2021 ◽  
pp. 174751982110325
Author(s):  
Yan Xiao ◽  
Jiyu Gao ◽  
Peng Chen ◽  
Guangliang Chen ◽  
Zicheng Li ◽  
...  
Keyword(s):  
Functional Group ◽  
Reaction Times ◽  
Environmentally Friendly ◽  
Solvent Free ◽  
Copper Salt ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
Solvent Free Conditions ◽  
Environmentally Friendly Process

A series of symmetrical 1,4-disubstituted buta-1,3-diynes is prepared with excellent yields (up to 95%) through homocoupling of terminal alkynes catalyzed by a copper salt under solvent-free conditions. This method provides an environmentally friendly process to prepare 1,3-diynes in short reaction times under mild conditions. Furthermore, the method is suitable for a wide substrate scope and has excellent functional group compatibility. The reaction can also be scaled up to gram level.

Acetylation of Alcohols and Amines under Visible Light Irradiation: Diacetyl as an Acylation Reagent and Photosensitizer

2021 ◽  
Author(s):  
Pengcheng Lian ◽  
Ruyi Li ◽  
Xiao Wan ◽  
Zixin Xiang ◽  
Hang Liu ◽  
...  
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Functional Group ◽  
Environmentally Friendly ◽  
Light Irradiation ◽  
Environmentally Friendly Process

This work developed an unprecedented strategy for the acetylation of alcohols and amines using diacetyl as both an acylation reagent and photosensitizer. This environmentally friendly process exhibits excellent functional group...

scholarly journals C–H and N–H Bond Annulation of Benzamides with Isonitriles Catalyzed by Cobalt(III)

Synthesis ◽  
2017 ◽  
Vol 49 (17) ◽  
pp. 3937-3944 ◽  
Author(s):  
Deepti Kalsi ◽  
Nagaraju Barsu ◽  
Pardeep Dahiya ◽  
Basker Sundararaju
Keyword(s):  
Functional Group ◽  
Bond Activation ◽  
Green Solvent ◽  
Tert Butyl ◽  
Mild Conditions

A simple efficient, atom-economical procedure was developed for the cobalt-catalyzed C–H bond annulation of benzamides with isonitriles under mild conditions. The reaction tolerates a variety of functional group including heterocycles. Diverse 3-(alkylimino)-2-quinolin-8-yl-2,3-dihydro-1H-isoindol-1-ones were synthesized using isonitriles as the C1 source through C–H and N–H bond annulation via C–H bond activation in a ‘green’ solvent. Vinylamides were also used similarly with tert-butyl isonitrile to give 3-(tert-butylimino)-1-quinolin-8-yl-1H-pyrrol-2(5H)-ones.

scholarly journals Nickel-Catalyzed Thiolation of Aryl Nitriles

2021 ◽  
Author(s):  
Tristan Delcaillau ◽  
Bill Morandi
Keyword(s):  
Late Stage ◽  
Functional Group ◽  
Bond Activation ◽  
Bond Formation ◽  
Aryl Nitriles

<div>A nickel-catalyzed thiolation of aryl nitriles has been developed to access functionalized aryl thioethers. The ligand dcype (1,2 Bis(dicyclohexylphosphino)ethane) as well as the base KOtBu (potassium tert-butoxide) are essential to achieve this transformation. This scalable and practical process involves both a C–C bond activation and a C–S bond formation. Furthermore, this reaction shows a high functional-group tolerance and enables the late-stage functionalization of important molecules.</div>

scholarly journals Enantioselective Palladium-Catalyzed C-C Bond Activation by Merging (3+2) Spiroannulation and Desymmetrization of Cyclic 1,3-Diketones

2021 ◽  
Author(s):  
Han-Qi Zhou ◽  
Xing-Wei Gu ◽  
Xiao-Hua Zhou ◽  
Li Li ◽  
Fei Ye ◽  
...  
Keyword(s):  
Functional Group ◽  
Bond Activation ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed ◽  
Catalytic Asymmetric

Catalytic asymmetric variants for the functional group-transformations based on carbon-carbon bond activation still remain elusive. Herein we present an unprecedented palladium-catalyzed (3+2) spiro-annulation that merging C(sp2)-C(sp2) s bond activation and...

Late-Stage Carbon Isotope Exchange of Aryl Nitriles through Ni-Catalyzed C–CN Bond Activation

2021 ◽  
Author(s):  
Sean Reilly ◽  
Yu-hong Lam ◽  
Sumei Ren ◽  
Neil Strotman
Keyword(s):  
Carbon Isotope ◽  
Late Stage ◽  
Isotope Exchange ◽  
Functional Group ◽  
Bond Activation ◽  
De Novo ◽  
Parent Compound ◽  
One Pot ◽  
Aryl Nitriles ◽  
Labeling Approach

<div> <p>A facile one-pot strategy for <sup>13</sup>CN and <sup>14</sup>CN exchange with aryl, heteroaryl, and vinyl nitriles using a Ni phosphine catalyst and BPh<sub>3</sub> is described. This late-stage carbon isotope exchange (CIE) strategy employs labeled Zn(CN)<sub>2</sub> to facilitate enrichment using the non-labeled parent compound as the starting material, eliminating <i>de novo</i> synthesis for precursor development. A broad substrate scope encompassing multiple pharmaceuticals is disclosed, including the preparation of [<sup>14</sup>C]<a>belzutifan</a> to illustrate the exceptional functional group tolerance and utility of this labeling approach. Preliminary experimental and computational studies suggest the Lewis acid BPh<sub>3</sub> is not critical for the oxidative addition step and instead plays a role in facilitating CN exchange on Ni. This CIE method dramatically reduces the synthetic steps and radioactive waste involved in preparation of <sup>14</sup>C labeled tracers for clinical development.</p> </div>

Ruthenium-Catalyzed Annulation of N-Cbz Hydrazones via C–H/N–N Bond Activation for the Rapid Synthesis of Isoquinolines

Synthesis ◽  
2019 ◽  
Vol 51 (12) ◽  
pp. 2506-2514 ◽  
Author(s):  
Dewal S. Deshmukh ◽  
Bhalchandra M. Bhanage
Keyword(s):  
Functional Group ◽  
Bond Activation ◽  
Strategy Use ◽  
Environmentally Benign ◽  
Catalyst Loading ◽  
Green Solvent ◽  
Rapid Synthesis ◽  
Ru Catalyst ◽  
Internal Alkynes ◽  
Directing Group

In this work, N-Cbz hydrazone has been employed as a rarely explored directing group for the synthesis of isoquinolines by annulation with internal alkynes via C–H/N–N activation using Ru catalyst. Additive as well as external oxidant-free rapid protocol has been established for the synthesis of isoquinolines using microwave strategy. Use of non-volatile and biodegradable PEG as a green solvent with lower catalyst loading makes the proposed protocol environmentally benign. Further, higher functional group tolerance and wide substrate scope has been observed under the stated methodology with higher yields.

scholarly journals The Enones as New Alkenyl Reagents via Ligand Promoted C–C Bonds Activation

2021 ◽  
Author(s):  
Hanyuan Li ◽  
Mei-Ling Wang ◽  
Yue-Wen Liu ◽  
Ling-Jun Li ◽  
Hui Xu ◽  
...  
Keyword(s):  
Natural Products ◽  
Late Stage ◽  
Functional Group ◽  
Bond Activation ◽  
Potential Utility ◽  
One Pot ◽  
Complex Molecules ◽  
The Past

Complementary to C–H bond activation, C–C bond activation has emerged over the past few years as an increasingly powerful tool to access and modify complex molecules. Ketones, owing to their versatility and availability, provide a significant platform for C–C bond activating reactions. Herein, we reported a <i>β</i>-carbon elimination strategy for alkene(sp<sup>2</sup>)–C(O) bonds to realize the olefination of unstrained enones via a vinyl palladium species, which delivers a series of conjugated polyene compounds. The protocol features broad substrate scope, excellent functional group tolerance and can be extended to dba (dibenzylideneacetone) substrates for olefination, alkynylation, arylation and amination, which demonstrates the generality of the approach and affords two valuable products in one pot. Furthermore, the late-stage functionalization of natural products (<i>β</i>-ionone and acetyl cedrene) and synthesis of natural products (piperine, lignarenone, novenone) highlight the potential utility of the reaction.

scholarly journals Late-Stage Carbon Isotope Exchange of Aryl Nitriles through Ni-Catalyzed C–CN Bond Activation

2021 ◽  
Author(s):  
Sean Reilly ◽  
Yu-hong Lam ◽  
Sumei Ren ◽  
Neil Strotman
Keyword(s):  
Carbon Isotope ◽  
Late Stage ◽  
Isotope Exchange ◽  
Functional Group ◽  
Bond Activation ◽  
De Novo ◽  
Parent Compound ◽  
One Pot ◽  
Aryl Nitriles ◽  
Labeling Approach

<div> <p>A facile one-pot strategy for <sup>13</sup>CN and <sup>14</sup>CN exchange with aryl, heteroaryl, and vinyl nitriles using a Ni phosphine catalyst and BPh<sub>3</sub> is described. This late-stage carbon isotope exchange (CIE) strategy employs labeled Zn(CN)<sub>2</sub> to facilitate enrichment using the non-labeled parent compound as the starting material, eliminating <i>de novo</i> synthesis for precursor development. A broad substrate scope encompassing multiple pharmaceuticals is disclosed, including the preparation of [<sup>14</sup>C]<a>belzutifan</a> to illustrate the exceptional functional group tolerance and utility of this labeling approach. Preliminary experimental and computational studies suggest the Lewis acid BPh<sub>3</sub> is not critical for the oxidative addition step and instead plays a role in facilitating CN exchange on Ni. This CIE method dramatically reduces the synthetic steps and radioactive waste involved in preparation of <sup>14</sup>C labeled tracers for clinical development.</p> </div>

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