Alkyl Tosylates as Alkylating Reagents in the Catellani Reaction

Qianwen Gao; Ze-Shui Liu; Yu Hua; Siwei Zhou; Hong-Gang Cheng; Qianghui Zhou

doi:10.1055/s-0039-1690801

Alkyl Tosylates as Alkylating Reagents in the Catellani Reaction

Synthesis ◽

10.1055/s-0039-1690801 ◽

2020 ◽

Vol 52 (06) ◽

pp. 834-846 ◽

Cited By ~ 2

Author(s):

Qianwen Gao ◽

Ze-Shui Liu ◽

Yu Hua ◽

Siwei Zhou ◽

Hong-Gang Cheng ◽

...

Keyword(s):

Catalytic System ◽

Aryl Iodides ◽

Alkylating Reagents

A cooperative catalytic system involving a Pd/XPhos complex and inexpensive 5-norbornene-2-carbonitrile that enables the use of alkyl tosylates as alkylating reagents in the Catellani reaction has been developed. This mild, scalable protocol is compatible with a range of readily available functionalized aryl iodides and alkyl tosylates, as well as terminating olefins (45 examples, up to 97% yield).

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Cu(I)-catalyzed N,N’-diarylation of natural diamines and polyamines with aryl iodides

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.11.250 ◽

2015 ◽

Vol 11 ◽

pp. 2297-2305 ◽

Cited By ~ 7

Author(s):

Svetlana Petrovna Panchenko ◽

Alexei Dmitrievich Averin ◽

Maksim Viktorovich Anokhin ◽

Olga Aleksandrovna Maloshitskaya ◽

Irina Petrovna Beletskaya

Keyword(s):

Catalytic System ◽

Aryl Iodides

The Cu(I)-catalyzed N,N’-diarylation of natural diamines and polyamines such as putrescine, cadaverine, spermine, spermidine and their homologues is described. Aryl iodides bearing electron-donating and electron-withdrawing groups have been employed in the study. The CuI/2-(isobutyryl)cyclohexanone/DMF catalytic system has found to be more efficient in the diarylation of diamines and spermine while the CuI/L-proline/EtCN system proved to be preferable for the diarylation of other tri- and tetraamines like spermidine, norspermidine and norspermine.

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A highly efficient copper and ligand free protocol for the room temperature Sonogashira reaction

RSC Advances ◽

10.1039/c4ra09630d ◽

2015 ◽

Vol 5 (1) ◽

pp. 16-19 ◽

Cited By ~ 16

Author(s):

Ankur Gogoi ◽

Anindita Dewan ◽

Utpal Bora

Keyword(s):

Catalytic System ◽

Room Temperature ◽

Sonogashira Reaction ◽

Highly Efficient ◽

Aryl Iodides ◽

Ligand Free

A mild and efficient catalytic system based on PdCl2 and Na2SO4 has been developed for the Sonogashira reaction of aryl iodides at room temperature.

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Epoxides as Dual-Functionalized Alkylating Reagents in Catellani Reactions for the Assembly of Heterocycles

Synlett ◽

10.1055/s-0039-1690779 ◽

2020 ◽

Vol 31 (09) ◽

pp. 829-837 ◽

Cited By ~ 1

Author(s):

Hong-Gang Cheng ◽

Qianghui Zhou ◽

Chenggui Wu

Keyword(s):

Carboxylic Acid ◽

Catalytic System ◽

Potassium Salt ◽

Salient Features ◽

Alkylating Reagents ◽

Straightforward Approach

Reported is a cooperative catalytic system consisting of a complex of Pd with dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPhos) and the potassium salt of 5-norbornene-2-carboxylic acid that permits the use of epoxides as dual-functionalized alkylating reagents in Catellani-type reactions for the assembly of heterocycles. Salient features of this research include readily available substrates, use of the potassium salt of 5-norbornene-2-carboxylic acid as a catalytic mediator as well as a base, and excellent regioselectivity for the cleavage of epoxides. This mild, chemoselective, scalable, atom- and step-economic protocol offers a straightforward approach for the assembly of isochroman and 2,3-dihydrobenzofuran scaffolds.

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Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.9.50 ◽

2013 ◽

Vol 9 ◽

pp. 467-475 ◽

Cited By ~ 26

Author(s):

Silvia M Soria-Castro ◽

Alicia B Peñéñory

Keyword(s):

Microwave Irradiation ◽

Microwave Heating ◽

Catalytic System ◽

Low Cost ◽

One Pot ◽

Alkyl Aryl ◽

One Pot Synthesis ◽

Aryl Iodides ◽

The One ◽

Aryl Sulfides

S-aryl thioacetates can be prepared by reaction of inexpensive potassium thioacetate with both electron-rich and electron-poor aryl iodides under a base-free copper/ligand catalytic system. CuI as copper source affords S-aryl thioacetates in good to excellent yields, by using 1,10-phenanthroline as a ligand in toluene at 100 °C after 24 h. Under microwave irradiation the time was drastically reduced to 2 h. Both procedures are simple and involve a low-cost catalytic system. This methodology was also applied to the “one-pot” synthesis of target heterocycles, such as 3H-benzo[c][1,2]dithiol-3-one and 2-methylbenzothiazole, alkyl aryl sulfides, diaryl disulfides and asymmetric diaryl sulfides in good yields.

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