Literature DB >> 27245257

Formation of C(sp(3) )-C(sp(3) ) Bonds through Nickel-Catalyzed Decarboxylative Olefin Hydroalkylation Reactions.

Xi Lu1,2, Bin Xiao1, Lei Liu2, Yao Fu3.   

Abstract

Olefins and carboxylic acids are among the most important feedstock compounds. They are commonly found in natural products and drug molecules. We report a new reaction of nickel-catalyzed decarboxylative olefin hydroalkylation, which provides a novel practical strategy for the construction of C(sp(3) )-C(sp(3) ) bonds. This reaction can tolerate a variety of synthetically relevant functional groups and shows good chemo- and regioselectivity. It enables cross-coupling of complex organic molecules containing olefin groups and carboxylic acid groups in a convergent fashion.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C bond formation; catalysis; decarboxylative cross-coupling; nickel; olefin hydroalkylation

Year:  2016        PMID: 27245257     DOI: 10.1002/chem.201602486

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


  7 in total

1.  Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides.

Authors:  Naoyuki Suzuki; Julie L Hofstra; Kelsey E Poremba; Sarah E Reisman
Journal:  Org Lett       Date:  2017-04-04       Impact factor: 6.005

2.  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

3.  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

4.  Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations.

Authors:  Shan Wang; Jian-Xin Zhang; Tian-Yi Zhang; Huan Meng; Bi-Hong Chen; Wei Shu
Journal:  Nat Commun       Date:  2021-05-13       Impact factor: 14.919

Review 5.  Radicals: Reactive Intermediates with Translational Potential.

Authors:  Ming Yan; Julian C Lo; Jacob T Edwards; Phil S Baran
Journal:  J Am Chem Soc       Date:  2016-09-26       Impact factor: 15.419

6.  Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions.

Authors:  Jing-Yu Guo; Ze-Yu Zhang; Ting Guan; Lei-Wen Mao; Qian Ban; Kai Zhao; Teck-Peng Loh
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

7.  Active template rotaxane synthesis through the Ni-catalyzed cross-coupling of alkylzinc reagents with redox-active esters.

Authors:  Javier Echavarren; Malcolm A Y Gall; Adrian Haertsch; David A Leigh; Vanesa Marcos; Daniel J Tetlow
Journal:  Chem Sci       Date:  2019-06-19       Impact factor: 9.825

  7 in total

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