Literature DB >> 28834053

Nickel-Catalyzed Reductive Allylation of Tertiary Alkyl Halides with Allylic Carbonates.

Haifeng Chen1, Xiao Jia1, Yingying Yu1, Qun Qian1, Hegui Gong1.   

Abstract

The construction of all C(sp3 ) quaternary centers has been successfully achieved under Ni-catalyzed cross-electrophile coupling of allylic carbonates with unactivated tertiary alkyl halides. For allylic carbonates bearing C1 or C3 substituents, the reaction affords excellent regioselectivity through the addition of alkyl groups to the unsubstituted allylic carbon terminus. The allylic alkylation method also exhibits excellent functional-group compatibility, and delivers the products with high E selectivity.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allylation; electrophiles; nickel; quaternary carbon centers; tertiary alkyl halides

Year:  2017        PMID: 28834053     DOI: 10.1002/anie.201705521

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


  14 in total

1.  Regioselective Single-Electron Tsuji-Trost Reaction of Allylic Alcohols: A Photoredox/Nickel Dual Catalytic Approach.

Authors:  Zheng-Jun Wang; Shuai Zheng; Eugénie Romero; Jennifer K Matsui; Gary A Molander
Journal:  Org Lett       Date:  2019-08-07       Impact factor: 6.005

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

Authors:  Quentin D Tercenio; Erik J Alexanian
Journal:  Org Lett       Date:  2021-08-31       Impact factor: 6.072

3.  Nickel-Catalyzed C(sp3)-C(sp3) Cross-Electrophile Coupling of In Situ Generated NHP Esters with Unactivated Alkyl Bromides.

Authors:  Kai Kang; Daniel J Weix
Journal:  Org Lett       Date:  2022-04-13       Impact factor: 6.072

4.  Integrating Allyl Electrophiles into Nickel-Catalyzed Conjunctive Cross-Coupling.

Authors:  Van T Tran; Zi-Qi Li; Timothy J Gallagher; Joseph Derosa; Peng Liu; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-13       Impact factor: 15.336

5.  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

6.  FeCl2-Mediated Rearrangement of Allylic Alcohols.

Authors:  Anita A Oppong-Quaicoe; Brenton DeBoef
Journal:  ACS Omega       Date:  2019-03-29

7.  Lewis Acid Catalyzed Transfer Hydromethallylation for the Construction of Quaternary Carbon Centers.

Authors:  Johannes C L Walker; Martin Oestreich
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-12       Impact factor: 15.336

8.  Nickel-catalyzed migratory alkyl-alkyl cross-coupling reaction.

Authors:  Yangyang Li; Yuqiang Li; Long Peng; Dong Wu; Lei Zhu; Guoyin Yin
Journal:  Chem Sci       Date:  2020-09-09       Impact factor: 9.825

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

Authors:  Zhiyang Lin; Youxiang Jin; Weitao Hu; Chuan Wang
Journal:  Chem Sci       Date:  2021-04-09       Impact factor: 9.825

10.  Reductive coupling of benzyl oxalates with highly functionalized alkyl bromides by nickel catalysis.

Authors:  Xiao-Biao Yan; Chun-Ling Li; Wen-Jie Jin; Peng Guo; Xing-Zhong Shu
Journal:  Chem Sci       Date:  2018-04-20       Impact factor: 9.825

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