Literature DB >> 31145628

Photoredox-Catalyzed Multicomponent Petasis Reaction with Alkyltrifluoroborates.

Jun Yi1,2, Shorouk O Badir1, Rauful Alam1, Gary A Molander1.   

Abstract

A redox-neutral alkyl Petasis reaction has been developed that proceeds via photoredox catalysis. A diverse set of primary, secondary, and tertiary alkyltrifluoroborates participate effectively in this reaction through a single-electron transfer mechanism, in contrast to the traditional two-electron Petasis reaction, which accommodates only unsaturated boronic acids. This protocol is ideal to diversify benzyl-type and glyoxalate-derived aldehydes, anilines, and alkyltrifluoroborates toward the rapid assembly of libraries of higher molecular complexity important in pharmaceutical and agrochemical settings.

Entities:  

Year:  2019        PMID: 31145628      PMCID: PMC7086342          DOI: 10.1021/acs.orglett.9b01747

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  44 in total

Review 1.  Diversity-oriented synthesis: producing chemical tools for dissecting biology.

Authors:  Cornelius J O' Connor; Henning S G Beckmann; David R Spring
Journal:  Chem Soc Rev       Date:  2012-04-10       Impact factor: 54.564

Review 2.  Chemistry and biology of multicomponent reactions.

Authors:  Alexander Dömling; Wei Wang; Kan Wang
Journal:  Chem Rev       Date:  2012-03-22       Impact factor: 60.622

Review 3.  Organocatalysed asymmetric Mannich reactions.

Authors:  Jorge M M Verkade; Lieke J C van Hemert; Peter J L M Quaedflieg; Floris P J T Rutjes
Journal:  Chem Soc Rev       Date:  2007-10-30       Impact factor: 54.564

4.  Umpolung Addition of Aldehydes to Aryl Imines.

Authors:  Ning Chen; Xi-Jie Dai; Haining Wang; Chao-Jun Li
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-27       Impact factor: 15.336

5.  Visible light-promoted alkylation of imines using potassium organotrifluoroborates.

Authors:  Davis P Plasko; Christopher J Jordan; Brittney E Ciesa; Madison A Merrill; James M Hanna
Journal:  Photochem Photobiol Sci       Date:  2018-05-16       Impact factor: 3.982

6.  Intermolecular alkyl radical additions to enantiopure N-tert-butanesulfinyl aldimines.

Authors:  José A Fernández-Salas; M Carmen Maestro; M Mercedes Rodríguez-Fernández; José L García-Ruano; Inés Alonso
Journal:  Org Lett       Date:  2013-03-13       Impact factor: 6.005

7.  Combination of organotrifluoroborates with photoredox catalysis marking a new phase in organic radical chemistry.

Authors:  Takashi Koike; Munetaka Akita
Journal:  Org Biomol Chem       Date:  2016-06-10       Impact factor: 3.876

8.  Deaminative Strategy for the Visible-Light-Mediated Generation of Alkyl Radicals.

Authors:  Felix J R Klauck; Michael J James; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-29       Impact factor: 15.336

9.  Metal-free C-H alkylation of heteroarenes with alkyltrifluoroborates: a general protocol for 1°, 2° and 3° alkylation.

Authors:  Jennifer K Matsui; David N Primer; Gary A Molander
Journal:  Chem Sci       Date:  2017-03-06       Impact factor: 9.825

10.  Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals.

Authors:  Eleonora Fava; Anthony Millet; Masaki Nakajima; Sebastian Loescher; Magnus Rueping
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-02       Impact factor: 15.336

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  9 in total

1.  Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes.

Authors:  Jonathan J Kennedy-Ellis; Erik D Boldt; Sherry R Chemler
Journal:  Org Lett       Date:  2020-10-19       Impact factor: 6.005

2.  Diastereo- and regioselective petasis aryl and allyl boration of ninhydrins towards synthesis of functionalized indene-diones and dihydrobenzoindeno-oxazin-ones.

Authors:  Ayon Sengupta; Suvendu Maity; Pinaki Saha; Prasanta Ghosh; Sonali Rudra; Chhanda Mukhopadhyay
Journal:  Mol Divers       Date:  2022-08-01       Impact factor: 3.364

3.  A General N-alkylation Platform via Copper Metallaphotoredox and Silyl Radical Activation of Alkyl Halides.

Authors:  Nathan W Dow; Albert Cabré; David W C MacMillan
Journal:  Chem       Date:  2021-06-16       Impact factor: 25.832

4.  A continuous-flow protocol for photoredox-catalyzed multicomponent Petasis reaction.

Authors:  Monica Oliva; Frederick Martens; Erik V Van der Eycken; Upendra Kumar Sharma
Journal:  STAR Protoc       Date:  2022-02-05

5.  Excited-state palladium-catalysed reductive alkylation of imines: scope and mechanism.

Authors:  Rajesh Kancherla; Krishnamoorthy Muralirajan; Magnus Rueping
Journal:  Chem Sci       Date:  2022-07-07       Impact factor: 9.969

Review 6.  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

7.  Preparation of α-amino acids via Ni-catalyzed reductive vinylation and arylation of α-pivaloyloxy glycine.

Authors:  Xianghua Tao; Yanchi Chen; Jiandong Guo; Xiaotai Wang; Hegui Gong
Journal:  Chem Sci       Date:  2020-10-27       Impact factor: 9.825

8.  Multicomponent Petasis Reaction for the Synthesis of Functionalized 2-Aminothiophenes and Thienodiazepines.

Authors:  Jimin Hwang; Lydia Borgelt; Peng Wu
Journal:  ACS Comb Sci       Date:  2020-09-28       Impact factor: 3.784

9.  Photoinduced 1,2-dicarbofunctionalization of alkenes with organotrifluoroborate nucleophiles via radical/polar crossover.

Authors:  María Jesús Cabrera-Afonso; Anasheh Sookezian; Shorouk O Badir; Mirna El Khatib; Gary A Molander
Journal:  Chem Sci       Date:  2021-06-07       Impact factor: 9.969

  9 in total

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