Literature DB >> 30623547

Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents.

Tie-Gen Chen1, Haolin Zhang1, Pavel K Mykhailiuk1,2,3, Rohan R Merchant1, Courtney A Smith1, Tian Qin1, Phil S Baran1.   

Abstract

This work bridges a gap in the cross-coupling of aliphatic redox-active esters with aryl zinc reagents. Previously limited to primary, secondary, and specialized tertiary centers, a new protocol has been devised to enable the coupling of general tertiary systems using nickel catalysis. The scope of this operationally simple method is broad, and it can be used to simplify the synthesis of medicinally relevant motifs bearing quaternary centers.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  decarboxylative radical coupling; nickel catalysis; quaternary centers; redox-active esters; tertiary acids

Year:  2019        PMID： 30623547      PMCID： PMC6391118          DOI： 10.1002/anie.201814524

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  33 in total

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Journal:  J Am Chem Soc       Date:  2012-06-26       Impact factor: 15.419

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Journal:  J Am Chem Soc       Date:  2015-09-03       Impact factor: 15.419

8.  Nickel-catalyzed carbon-carbon bond-forming reactions of unactivated tertiary alkyl halides: Suzuki arylations.

Authors:  Susan L Zultanski; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2013-01-02       Impact factor: 15.419

9.  Copper-catalyzed cross-coupling of functionalized alkyl halides and tosylates with secondary and tertiary alkyl Grignard reagents.

Authors:  Peng Ren; Lucas-Alexandre Stern; Xile Hu
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-31       Impact factor: 15.336

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Journal:  J Am Chem Soc       Date:  2019-04-16       Impact factor: 15.419

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4.  Electrochemical Decarboxylative N-Alkylation of Heterocycles.

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Authors:  Julia R Dorsheimer; Melissa A Ashley; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2021-11-12       Impact factor: 15.419

6.  Convergent Synthesis of (R)-Silodosin via Decarboxylative Cross-Coupling.

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7.  On the Nature of C(sp3)-C(sp2) Bond Formation in Nickel-Catalyzed Tertiary Radical Cross-Couplings: A Case Study of Ni/Photoredox Catalytic Cross-Coupling of Alkyl Radicals and Aryl Halides.

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Journal:  J Am Chem Soc       Date:  2020-04-01       Impact factor: 15.419

8.  Evolution of a Strategy for the Enantioselective Synthesis of (-)-Cajanusine.

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Journal:  J Am Chem Soc       Date:  2020-03-09       Impact factor: 15.419

9.  Hydroalkylation of Olefins To Form Quaternary Carbons.

Authors:  Samantha A Green; Tucker R Huffman; Ruairí O McCourt; Vincent van der Puyl; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2019-05-03       Impact factor: 15.419

10.  1,2-Difunctionalized bicyclo[1.1.1]pentanes: Long-sought-after mimetics for ortho/meta-substituted arenes.

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Journal:  Proc Natl Acad Sci U S A       Date:  2021-07-13       Impact factor: 11.205
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