Literature DB >> 32884161

Cobalt(III)-Catalyzed Diastereoselective Three-Component C-H Bond Addition to Butadiene and Activated Ketones.

Zican Shen1, Chen Li1, Brandon Q Mercado1, Jonathan A Ellman1.   

Abstract

A highly diastereoselective three-component C-H bond addition across butadiene and activated ketones is described. This transformation provides homoallylic tertiary alcohols through the formation of two C-C σ bonds and with complete selectivity for an E-alkene isomer. The reaction exhibits good scope with respect to activated ketone inputs, including highly strained cyclic and electron-deficient cyclic and acyclic ketones. Additionally, high diastereoselectivities were achieved for alcohols prepared from unsymmetrical ketones.

Entities:  

Keywords:  C–H activation; cobalt; diastereoselectivity; homogeneous catalysis; ketones; multicomponent reaction

Year:  2019        PMID： 32884161      PMCID： PMC7462114          DOI： 10.1055/s-0039-1690741

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  21 in total

1.  3d Transition Metals for C-H Activation.

Authors:  Parthasarathy Gandeepan; Thomas Müller; Daniel Zell; Gianpiero Cera; Svenja Warratz; Lutz Ackermann
Journal:  Chem Rev       Date:  2018-11-27       Impact factor: 60.622

2.  Metal-Organic Cooperative Catalysis in C-H and C-C Bond Activation.

Authors:  Dong-Su Kim; Woo-Jin Park; Chul-Ho Jun
Journal:  Chem Rev       Date:  2017-01-06       Impact factor: 60.622

3.  Palladium/Norbornene Cooperative Catalysis.

Authors:  Jianchun Wang; Guangbin Dong
Journal:  Chem Rev       Date:  2019-04-25       Impact factor: 60.622

4.  A Convergent Synthesis of Functionalized Alkenyl Halides through Cobalt(III)-Catalyzed Three-Component C-H Bond Addition.

Authors:  Jeffrey A Boerth; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-17       Impact factor: 15.336

5.  Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds.

Authors:  Joshua R Hummel; Jeffrey A Boerth; Jonathan A Ellman
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

6.  Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII -Catalyzed Three-Component C-H Bond Addition to Internally Substituted Dienes and Carbonyls.

Authors:  Sun Dongbang; Zican Shen; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-01       Impact factor: 15.336

Review 7.  C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.

Authors:  Junichiro Yamaguchi; Atsushi D Yamaguchi; Kenichiro Itami
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-06       Impact factor: 15.336

8.  Palladium-catalysed norbornene-mediated C-H functionalization of arenes.

Authors:  Juntao Ye; Mark Lautens
Journal:  Nat Chem       Date:  2015-11       Impact factor: 24.427

9.  Rh(III)-Catalyzed Diastereoselective C-H Bond Addition/Cyclization Cascade of Enone Tethered Aldehydes.

Authors:  Jeffrey A Boerth; Jonathan A Ellman
Journal:  Chem Sci       Date:  2015-12-01       Impact factor: 9.825

10.  Cobalt-catalyzed hydroxymethylarylation of terpenes with formaldehyde and arenes.

Authors:  Jun Yang; Ding-Wei Ji; Yan-Cheng Hu; Xiang-Ting Min; Xiangge Zhou; Qing-An Chen
Journal:  Chem Sci       Date:  2019-08-26       Impact factor: 9.825
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  2 in total

Review 1.  C-H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity.

Authors:  Daniel S Brandes; Jonathan A Ellman
Journal:  Chem Soc Rev       Date:  2022-08-01       Impact factor: 60.615

2.  Stereoselective Synthesis of Allenyl Alcohols by Cobalt(III)-Catalyzed Sequential C-H Bond Addition to 1,3-Enynes and Aldehydes.

Authors:  Chaofan Xu; Joseph P Tassone; Brandon Q Mercado; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-29       Impact factor: 16.823
  2 in total

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