Literature DB >> 35464106

Catalytic Arylboration of Spirocyclic Cyclobutenes: Rapid Access to Highly Substituted Spiro[3.n]alkanes.

Amit Kumar Simlandy1, Mao-Yun Lyu1, M Kevin Brown1.   

Abstract

A method to achieve the synthesis of highly substituted spirocyclic cyclobutanes is disclosed. The reaction involves the catalytic arylboration of cyclobutenes. Depending on the substitution pattern of the cyclobutene, either a Cu/Pd- or a Ni-catalyzed reaction was utilized. In the case of the Cu/Pd catalyzed reactions, the identification of a Cu-complex for arylboration was crucial to observe high selectivity. The synthetic utility of the products is demonstrated, and the mechanistic details are discussed.

Entities:  

Keywords:  arylboration; boron; copper; nickel; palladium

Year:  2021        PMID: 35464106      PMCID: PMC9031217          DOI: 10.1021/acscatal.1c03491

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.700


  45 in total

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Authors:  Ramon Rios
Journal:  Chem Soc Rev       Date:  2011-10-05       Impact factor: 54.564

Review 2.  The use of spirocyclic scaffolds in drug discovery.

Authors:  Yajun Zheng; Colin M Tice; Suresh B Singh
Journal:  Bioorg Med Chem Lett       Date:  2014-07-05       Impact factor: 2.823

3.  Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

Authors:  Kaitlyn M Logan; Stephen R Sardini; Sean D White; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-12-22       Impact factor: 15.419

Review 4.  Spirocyclic Scaffolds in Medicinal Chemistry.

Authors:  Kerstin Hiesinger; Dmitry Dar'in; Ewgenij Proschak; Mikhail Krasavin
Journal:  J Med Chem       Date:  2020-12-31       Impact factor: 7.446

5.  Alkene carboboration enabled by synergistic catalysis.

Authors:  Kevin B Smith; Kaitlyn M Logan; Wei You; M Kevin Brown
Journal:  Chemistry       Date:  2014-08-11       Impact factor: 5.236

6.  Nickel-Catalyzed Arylboration of Alkenylarenes: Synthesis of Boron-Substituted Quaternary Carbons and Regiodivergent Reactions.

Authors:  Liang-An Chen; Alan R Lear; Pin Gao; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-28       Impact factor: 15.336

7.  Stereospecific functionalizations and transformations of secondary and tertiary boronic esters.

Authors:  Christopher Sandford; Varinder K Aggarwal
Journal:  Chem Commun (Camb)       Date:  2017-05-17       Impact factor: 6.222

8.  Escape from flatland: increasing saturation as an approach to improving clinical success.

Authors:  Frank Lovering; Jack Bikker; Christine Humblet
Journal:  J Med Chem       Date:  2009-11-12       Impact factor: 7.446

9.  Design and Preparation of New Palladium Precatalysts for C-C and C-N Cross-Coupling Reactions.

Authors:  Nicholas C Bruno; Matthew T Tudge; Stephen L Buchwald
Journal:  Chem Sci       Date:  2013       Impact factor: 9.825

10.  Mechanism-Based Design of an Amide-Directed Ni-Catalyzed Arylboration of Cyclopentene Derivatives.

Authors:  Alison L Lambright; Yanyao Liu; Isaac A Joyner; Kaitlyn M Logan; M Kevin Brown
Journal:  Org Lett       Date:  2021-01-04       Impact factor: 6.005

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  2 in total

1.  Cooperative Pd/Cu Catalysis for Alkene Arylboration: Opportunities for Divergent Reactivity.

Authors:  Stanna K Dorn; M Kevin Brown
Journal:  ACS Catal       Date:  2022-01-24       Impact factor: 13.700

2.  Photosensitized [2+2]-Cycloadditions of Alkenylboronates and Alkenes.

Authors:  Yanyao Liu; Dongshun Ni; Bernard G Stevenson; Vikrant Tripathy; Sarah E Braley; Krishnan Raghavachari; John R Swierk; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-21       Impact factor: 16.823

  2 in total

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