Literature DB >> 35446458

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

Yanyao Liu1, Dongshun Ni1, Bernard G Stevenson2, Vikrant Tripathy1, Sarah E Braley1, Krishnan Raghavachari1, John R Swierk2, M Kevin Brown1.   

Abstract

A new strategy for the synthesis of highly versatile cyclobutylboronates via the photosensitized [2+2]-cycloaddition of alkenylboronates and alkenes is presented. The process is mechanistically different from other processes in that energy transfer occurs with the alkenylboronate as opposed to the other alkene. This strategy allows for the synthesis of an array of diverse cyclobutylboronates. The conversion of these adducts to other compounds as well as their utility in the synthesis of melicodenine C is demonstrated.
© 2022 Wiley-VCH GmbH.

Entities:  

Year:  2022        PMID： 35446458      PMCID： PMC9189050          DOI： 10.1002/anie.202200725

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   16.823


  56 in total

Review 1.  Positional and Geometrical Isomerisation of Alkenes: The Pinnacle of Atom Economy.

Authors:  John J Molloy; Tobias Morack; Ryan Gilmour
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-08       Impact factor: 15.336

2.  Enantioselective catalysis of photochemical reactions.

Authors:  Richard Brimioulle; Dominik Lenhart; Mark M Maturi; Thorsten Bach
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-27       Impact factor: 15.336

3.  Enantioselective photochemistry through Lewis acid-catalyzed triplet energy transfer.

Authors:  Travis R Blum; Zachary D Miller; Desiree M Bates; Ilia A Guzei; Tehshik P Yoon
Journal:  Science       Date:  2016-12-16       Impact factor: 47.728

4.  Catalytic Enantioselective Synthesis of Cyclobutenes from Alkynes and Alkenyl Derivatives.

Authors:  Mahesh M Parsutkar; Vinayak Vishnu Pagar; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

5.  Synthesis of Cyclobutane-Fused Angular Tetracyclic Spiroindolines via Visible-Light-Promoted Intramolecular Dearomatization of Indole Derivatives.

Authors:  Min Zhu; Chao Zheng; Xiao Zhang; Shu-Li You
Journal:  J Am Chem Soc       Date:  2019-01-31       Impact factor: 15.419

6.  High-Throughput Ligand Screening Enables the Enantioselective Conjugate Borylation of Cyclobutenones to Access Synthetically Versatile Tertiary Cyclobutylboronates.

Authors:  Helen A Clement; Michele Boghi; Rory M McDonald; Louise Bernier; Jotham W Coe; William Farrell; Christopher J Helal; Matthew R Reese; Neal W Sach; Jack C Lee; Dennis G Hall
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-31       Impact factor: 15.336

7.  Intramolecular Crossed [2+2] Photocycloaddition through Visible Light-Induced Energy Transfer.

Authors:  Jiannan Zhao; Jonathan L Brosmer; Qingxuan Tang; Zhongyue Yang; K N Houk; Paula L Diaconescu; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2017-07-11       Impact factor: 15.419

8.  Intermolecular Crossed [2 + 2] Cycloaddition Promoted by Visible-Light Triplet Photosensitization: Expedient Access to Polysubstituted 2-Oxaspiro[3.3]heptanes.

Authors:  Philip R D Murray; Willem M M Bussink; Geraint H M Davies; Farid W van der Mei; Alyssa H Antropow; Jacob T Edwards; Laura Akullian D'Agostino; J Michael Ellis; Lawrence G Hamann; Fedor Romanov-Michailidis; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2021-03-05       Impact factor: 15.419

9.  Direct Visible-Light-Excited Asymmetric Lewis Acid Catalysis of Intermolecular [2+2] Photocycloadditions.

Authors:  Xiaoqiang Huang; Taylor R Quinn; Klaus Harms; Richard D Webster; Lilu Zhang; Olaf Wiest; Eric Meggers
Journal:  J Am Chem Soc       Date:  2017-06-29       Impact factor: 15.419

10.  Brønsted acid catalysis of photosensitized cycloadditions.

Authors:  Evan M Sherbrook; Hoimin Jung; Dasol Cho; My-Hyun Baik; Tehshik P Yoon
Journal:  Chem Sci       Date:  2019-12-02       Impact factor: 9.825
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  2 in total

1.  Cascade cyclization of alkene-tethered acylsilanes and allylic sulfones enabled by unproductive energy transfer photocatalysis.

Authors:  Yunxiao Zhang; Yizhi Zhang; Chen Ye; Xiaotian Qi; Li-Zhu Wu; Xiao Shen
Journal:  Nat Commun       Date:  2022-10-16       Impact factor: 17.694

Review 2.  The Impact of Boron Hybridisation on Photocatalytic Processes.

Authors:  Alessandro Marotta; Callum E Adams; John J Molloy
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-10       Impact factor: 16.823
  2 in total

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