Literature DB >> 31604006

Accessing 1,2-Substituted Cyclobutanes through 1,2-Azaborine Photoisomerization.

Zachary X Giustra1, Xinyu Yang1, Min Chen1, Holger F Bettinger2, Shih-Yuan Liu1.   

Abstract

We provide a seminal example of the utility of the 1,2-azaborine motif as a 4C+1N+1B synthon in organic synthesis. Specifically, conditions for the practically scalable photoisomerization of 1,2-azaborine in a flow reactor are reported that furnish aminoborylated cyclobutane derivatives. The C-B bonds could also be functionalized to furnish a diverse set of highly substituted cyclobutanes.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  boron-nitrogen heterocycles; flow chemistry; photochemistry; small ring systems; valence isomerization

Mesh：

Substances：

Year:  2019        PMID： 31604006      PMCID： PMC6917847          DOI： 10.1002/anie.201912132

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


  46 in total

1.  Late-Stage Functionalization of 1,2-Dihydro-1,2-azaborines via Regioselective Iridium-Catalyzed C-H Borylation: The Development of a New N,N-Bidentate Ligand Scaffold.

Authors:  Andrew W Baggett; Monica Vasiliu; Bo Li; David A Dixon; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2015-04-20       Impact factor: 15.419

2.  Medicinal Chemistry Profiling of Monocyclic 1,2-Azaborines.

Authors:  Peng Zhao; David O Nettleton; Rajeshri G Karki; Frédéric J Zécri; Shih-Yuan Liu
Journal:  ChemMedChem       Date:  2017-02-21       Impact factor: 3.466

3.  Preparation of organotrifluoroborate salts: precipitation-driven equilibrium under non-etching conditions.

Authors:  Alastair J J Lennox; Guy C Lloyd-Jones
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-17       Impact factor: 15.336

4.  Photochemical transformations accelerated in continuous-flow reactors: basic concepts and applications.

Authors:  Yuanhai Su; Natan J W Straathof; Volker Hessel; Timothy Noël
Journal:  Chemistry       Date:  2014-07-23       Impact factor: 5.236

5.  Stereospecific synthesis of cyclobutylboronates through copper(I)-catalyzed reaction of homoallylic sulfonates and a diboron derivative.

Authors:  Hajime Ito; Takashi Toyoda; Masaya Sawamura
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

6.  Enantioselective Synthesis of Cyclobutylboronates via a Copper-Catalyzed Desymmetrization Approach.

Authors:  Manuel Guisán-Ceinos; Alejandro Parra; Víctor Martín-Heras; Mariola Tortosa
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-09       Impact factor: 15.336

7.  Regioregular synthesis of azaborine oligomers and a polymer with a syn conformation stabilized by N-H⋅⋅⋅π interactions.

Authors:  Andrew W Baggett; Fang Guo; Bo Li; Shih-Yuan Liu; Frieder Jäkle
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-14       Impact factor: 15.336

8.  1,2-Azaborine's Distinct Electronic Structure Unlocks Two New Regioisomeric Building Blocks via Resolution Chemistry.

Authors:  Cameron R McConnell; Fredrik Haeffner; Andrew W Baggett; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2019-05-23       Impact factor: 15.419

9.  Pd(II)-Catalyzed Enantioselective C(sp3)-H Borylation.

Authors:  Jian He; Qian Shao; Qingfeng Wu; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2017-02-23       Impact factor: 15.419

10.  1,2-Azaborine cations.

Authors:  Adam J V Marwitz; Jesse T Jenkins; Lev N Zakharov; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2010-10-04       Impact factor: 15.336
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  5 in total

1.  Multifaceted Substrate-Ligand Interactions Promote the Copper-Catalyzed Hydroboration of Benzylidenecyclobutanes and Related Compounds.

Authors:  Taeho Kang; Tuğçe G Erbay; Kane L Xu; Gary M Gallego; Alexander Burtea; Sajiv K Nair; Ryan L Patman; Ru Zhou; Scott C Sutton; Indrawan J McAlpine; Peng Liu; Keary M Engle
Journal:  ACS Catal       Date:  2020-10-27       Impact factor: 13.084

Review 2.  Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

Authors:  Laura Buglioni; Fabian Raymenants; Aidan Slattery; Stefan D A Zondag; Timothy Noël
Journal:  Chem Rev       Date:  2021-08-10       Impact factor: 60.622

3.  The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound.

Authors:  Yao Liu; Raimon Puig de la Bellacasa; Bo Li; Ana Belén Cuenca; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2021-08-25       Impact factor: 16.383

4.  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

5.  Construction of Complex Cyclobutane Building Blocks by Photosensitized [2 + 2] Cycloaddition of Vinyl Boronate Esters.

Authors:  Spencer O Scholz; Jesse B Kidd; Luca Capaldo; Niecia E Flikweert; Rowan M Littlefield; Tehshik P Yoon
Journal:  Org Lett       Date:  2021-04-12       Impact factor: 6.005
  5 in total

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