Literature DB >> 30521697

Catalyst-Controlled 1,2- and 1,1-Arylboration of α-Alkyl Alkenyl Arenes.

Allison M Bergmann1, Stanna K Dorn1, Kevin B Smith1, Kaitlyn M Logan1, M Kevin Brown1.   

Abstract

Two methods are reported for the 1,2- and 1,1-arylboration of α-methyl vinyl arenes. In the case of 1,2-arylboration, the formation of a quaternary center occurred through a rare cross-coupling reaction of a tertiary organometallic complex. 1,1-Arylboration was enabled by catalyst optimization and occurred through a β-hydride elimination/reinsertion cascade. Enantioselective variants of both processes are presented as well as mechanistic investigations.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carboboration; copper; cross-coupling; homogeneous catalysis; palladium

Mesh：

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Year:  2019        PMID： 30521697      PMCID： PMC6823597          DOI： 10.1002/anie.201812533

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


  42 in total

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3.  NHC-Cu-catalyzed enantioselective hydroboration of acyclic and exocyclic 1,1-disubstituted aryl alkenes.

Authors:  Rosa Corberán; Nicholas W Mszar; Amir H Hoveyda
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Authors:  Kevin B Smith; Kaitlyn M Logan; Wei You; M Kevin Brown
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5.  Sterically Controlled Cu-Catalyzed or Transition-Metal-Free Cross-Coupling of gem-Difluoroalkenes with Tertiary, Secondary, and Primary Alkyl Grignard Reagents.

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Journal:  Org Lett       Date:  2016-08-19       Impact factor: 6.005

6.  Regioselective Arylboration of Isoprene and Its Derivatives by Pd/Cu Cooperative Catalysis.

Authors:  Kevin B Smith; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-06-05       Impact factor: 15.419

7.  Copper-catalyzed alkyl-alkyl cross-coupling reactions using hydrocarbon additives: efficiency of catalyst and roles of additives.

Authors:  Takanori Iwasaki; Reiko Imanishi; Ryohei Shimizu; Hitoshi Kuniyasu; Jun Terao; Nobuaki Kambe
Journal:  J Org Chem       Date:  2014-07-10       Impact factor: 4.354

8.  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

9.  Copper-catalyzed cross-coupling of functionalized alkyl halides and tosylates with secondary and tertiary alkyl Grignard reagents.

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  18 in total

1.  Differential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling.

Authors:  Megan K Armstrong; Gojko Lalic
Journal:  J Am Chem Soc       Date:  2019-04-03       Impact factor: 15.419

2.  Ni-Catalyzed Arylboration of Unactivated Alkenes: Scope and Mechanistic Studies.

Authors:  Stephen R Sardini; Alison L Lambright; Grace L Trammel; Humair M Omer; Peng Liu; M Kevin Brown
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3.  (Hetero)arylboration of alkynes: a strategy for the synthesis of α,α-bis(hetero)arylketones.

Authors:  Yuan Huang; Allison M Bergmann; M Kevin Brown
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Journal:  ACS Catal       Date:  2019-10-29       Impact factor: 13.084

5.  Synthesis of Bisheteroarylalkanes by Heteroarylboration: Development and Application of a Pyridylidene-Copper Complex.

Authors:  Yuan Huang; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-27       Impact factor: 15.336

6.  Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid.

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7.  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
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Review 8.  Walking metals: catalytic difunctionalization of alkenes at nonclassical sites.

Authors:  Roshan K Dhungana; Rishi R Sapkota; Doleshwar Niroula; Ramesh Giri
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

9.  Modular Synthesis of a Versatile Double-Allylation Reagent for Complex Diol Synthesis.

Authors:  Stanna K Dorn; Annika E Tharp; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-11       Impact factor: 16.823

10.  Cyclic (Alkyl)(amino)carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes*.

Authors:  Yang Gao; Sima Yazdani; Aaron Kendrick; Glen P Junor; Taeho Kang; Douglas B Grotjahn; Guy Bertrand; Rodolphe Jazzar; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-29       Impact factor: 16.823
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