Literature DB >> 27101157

Silicon Amine Reagents for the Photocatalytic Synthesis of Piperazines from Aldehydes and Ketones.

Sheng-Ying Hsieh1, Jeffrey W Bode1.   

Abstract

Silicon amine protocol (SLAP) reagents for photocatalytic cross-coupling with aldehydes and ketones to form N-unprotected piperazines have been developed. This blue light promoted process tolerates a wide range of heteroaromatic, aromatic, and aliphatic aldehydes and structurally and stereochemically complex SLAP reagents. It provides a tin-free alternative to SnAP (tin amine protocol) reagents for the synthesis of substituted piperazines.

Entities:  

Year:  2016        PMID： 27101157     DOI： 10.1021/acs.orglett.6b00722

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


  11 in total

1.  Aminomethylation of Aryl Halides using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis.

Authors:  Camille Remeur; Christopher B Kelly; Niki R Patel; Gary A Molander
Journal:  ACS Catal       Date:  2017-08-16       Impact factor: 13.084

2.  Photoredox Radical/Polar Crossover Enables Construction of Saturated Nitrogen Heterocycles.

Authors:  Loïc R E Pantaine; John A Milligan; Jennifer K Matsui; Christopher B Kelly; Gary A Molander
Journal:  Org Lett       Date:  2019-03-12       Impact factor: 6.005

Review 3.  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

4.  Lewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement.

Authors:  Jeewani P Ariyarathna; Nur-E Alom; Leo P Roberts; Navdeep Kaur; Fan Wu; Wei Li
Journal:  J Org Chem       Date:  2022-02-10       Impact factor: 4.198

5.  Photoredox Generation of Carbon-Centered Radicals Enables the Construction of 1,1-Difluoroalkene Carbonyl Mimics.

Authors:  Simon B Lang; Rebecca J Wiles; Christopher B Kelly; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-24       Impact factor: 15.336

6.  Lewis Acid Induced Toggle from Ir(II) to Ir(IV) Pathways in Photocatalytic Reactions: Synthesis of Thiomorpholines and Thiazepanes from Aldehydes and SLAP Reagents.

Authors:  Sheng-Ying Hsieh; Jeffrey W Bode
Journal:  ACS Cent Sci       Date:  2016-12-29       Impact factor: 14.553

7.  Mild, Redox-Neutral Alkylation of Imines Enabled by an Organic Photocatalyst.

Authors:  Niki R Patel; Christopher B Kelly; Allison P Siegenfeld; Gary A Molander
Journal:  ACS Catal       Date:  2017-02-06       Impact factor: 13.084

Review 8.  Recent progress toward the asymmetric synthesis of carbon-substituted piperazine pharmacophores and oxidative related heterocycles.

Authors:  Plato A Magriotis
Journal:  RSC Med Chem       Date:  2020-05-22

9.  Expedient syntheses of N-heterocycles via intermolecular amphoteric diamination of allenes.

Authors:  Zhishi Ye; Sarju Adhikari; Yu Xia; Mingji Dai
Journal:  Nat Commun       Date:  2018-02-19       Impact factor: 14.919

10.  Expedient access to saturated nitrogen heterocycles by photoredox cyclization of imino-tethered dihydropyridines.

Authors:  Noah B Bissonnette; J Michael Ellis; Lawrence G Hamann; Fedor Romanov-Michailidis
Journal:  Chem Sci       Date:  2019-08-28       Impact factor: 9.825
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