Literature DB >> 29992705

Regiodivergent Copper Catalyzed Borocyanation of 1,3-Dienes.

Tao Jia1,2, Qiong He1, Rebecca E Ruscoe1, Alexander P Pulis1, David J Procter1.   

Abstract

Copper catalyzed multi-functionalization of unsaturated carbon-carbon bonds is a powerful tool for the generation of complex molecules. We report a regiodivergent process that allows a switch between 1,4-borocupration and 4,1-borocupration of 1,3-dienes upon a simple change in ligand. The subsequently generated allyl coppers are trapped in an electrophilic cyanation to selectively generate densely functionalized and synthetically versatile 1,2- or 4,3-borocyanation products.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  boron; catalysis; copper; multicomponent reactions; regioselectivity

Year:  2018        PMID： 29992705     DOI： 10.1002/anie.201806169

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


  10 in total

1.  Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

Authors:  Zhen Liu; Yang Gao; Tian Zeng; Keary M Engle
Journal:  Isr J Chem       Date:  2019-09-10       Impact factor: 3.333

2.  Racemic Vinylallenes in Catalytic Enantioselective Multicomponent Processes: Rapid Generation of Complexity through 1,6-Conjugate Additions.

Authors:  Youming Huang; Sebastian Torker; Xinghan Li; Juan Del Pozo; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-06       Impact factor: 15.336

3.  Pyridine(diimine) Iron Diene Complexes Relevant to Catalytic [2+2]-Cycloaddition Reactions.

Authors:  C Rose Kennedy; Hongyu Zhong; Matthew V Joannou; Paul J Chirik
Journal:  Adv Synth Catal       Date:  2019-11-19       Impact factor: 5.837

4.  Ligand-Controlled Regiodivergent Enantioselective Rhodium-Catalyzed Alkene Hydroboration.

Authors:  Andrew J Bochat; Veronika M Shoba; James M Takacs
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-06       Impact factor: 15.336

5.  Copper(I)-Catalyzed Asymmetric Conjugate 1,6-, 1,8-, and 1,10-Borylation.

Authors:  Chang-Yun Shi; Jungmin Eun; Timothy R Newhouse; Liang Yin
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-18       Impact factor: 15.336

Review 6.  Recent advances in Cu-catalyzed C(sp3)-Si and C(sp3)-B bond formation.

Authors:  Balaram S Takale; Ruchita R Thakore; Elham Etemadi-Davan; Bruce H Lipshutz
Journal:  Beilstein J Org Chem       Date:  2020-04-15       Impact factor: 2.883

7.  Catalyst-controlled selective borocarbonylation of benzylidenecyclopropanes: regiodivergent synthesis of γ-vinylboryl ketones and β-cyclopropylboryl ketones.

Authors:  Fu-Peng Wu; Xiao-Feng Wu
Journal:  Chem Sci       Date:  2022-03-21       Impact factor: 9.825

Review 8.  Copper-catalyzed functionalization of enynes.

Authors:  Quentin Dherbassy; Srimanta Manna; Fabien J T Talbot; Watcharapon Prasitwatcharakorn; Gregory J P Perry; David J Procter
Journal:  Chem Sci       Date:  2020-10-07       Impact factor: 9.825

Review 9.  Copper-Catalyzed Borylative Couplings with C-N Electrophiles.

Authors:  Fabien J T Talbot; Quentin Dherbassy; Srimanta Manna; Chunling Shi; Shibo Zhang; Gareth P Howell; Gregory J P Perry; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-28       Impact factor: 15.336

10.  Synthesis of Nitrile Bearing Acyclic Quaternary Centers through Co(III)-Catalyzed Sequential C-H Bond Addition to Dienes and N-Cyanosuccinimide.

Authors:  Sun Dongbang; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-23       Impact factor: 15.336
  10 in total

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