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Literature DB >> 22170740

Ni-catalyzed reductive allylation of unactivated alkyl halides with allylic carbonates.

Yijing Dai¹, Fan Wu, Zhenhua Zang, Hengzhi You, Hegui Gong.

Abstract

Game of two electrophiles: Two partially positively charged sp(3) carbon atoms can be connected by using a catalytic Ni species in the presence of an environmentally benign Zn reductant, delivering allylated alkanes. This unprecedented approach allowed a variety of unactivated alkyl halides and substituted allylic carbonates to regioselectively afford E-alkenes in good to excellent yields.

Entities: Chemical

Year: 2011 PMID： 22170740 DOI： 10.1002/chem.201102984

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

10 in total

1. Nickel-catalyzed reductive conjugate addition to enones via allylnickel intermediates.

Authors: Ruja Shrestha; Stephanie C M Dorn; Daniel J Weix
Journal: J Am Chem Soc Date: 2013-01-08 Impact factor: 15.419

2. Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides.

Authors: Daniel A Everson; Joseph A Buonomo; Daniel J Weix
Journal: Synlett Date: 2014-01 Impact factor: 2.454

3. Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes.

Authors: Amberly B Sanford; Taylor A Thane; Tristan M McGinnis; Pan-Pan Chen; Xin Hong; Elizabeth R Jarvo
Journal: J Am Chem Soc Date: 2020-03-04 Impact factor: 15.419

4. Acetate as a model for aspartate-based CXCR4 chemokine receptor binding of cobalt and nickel complexes of cross-bridged tetraazamacrocycles.

Authors: Amy N Cain; TaRynn N Carder Freeman; Kimberly D Roewe; David L Cockriel; Travis R Hasley; Randall D Maples; Elisabeth M A Allbritton; Thomas D'Huys; Tom van Loy; Benjamin P Burke; Timothy J Prior; Dominique Schols; Stephen J Archibald; Timothy J Hubin
Journal: Dalton Trans Date: 2019-02-19 Impact factor: 4.390

Ni-catalyzed reductive allylation of unactivated alkyl halides with allylic carbonates.

1. Nickel-catalyzed reductive conjugate addition to enones via allylnickel intermediates.

2. Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides.

3. Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes.

4. Acetate as a model for aspartate-based CXCR4 chemokine receptor binding of cobalt and nickel complexes of cross-bridged tetraazamacrocycles.

5. Stereospecific Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Tosylate and Allyl Alcohol Electrophiles.

6. Selective cross-coupling of organic halides with allylic acetates.

7. Mechanisms of Nickel-Catalyzed Coupling Reactions and Applications in Alkene Functionalization.

8. Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes.

9. Cross-electrophile coupling: principles of reactivity and selectivity.

10. Nickel-catalyzed asymmetric reductive cross-coupling between vinyl and benzyl electrophiles.