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Literature DB >> 29177314

Distal radical migration strategy: an emerging synthetic means.

Weipeng Li¹, Wentao Xu, Jin Xie, Shouyun Yu, Chengjian Zhu.

Abstract

The remote radical migration strategy has gained considerable momentum. During the past three years, we have witnessed the rapid development of sustainable and practical C-C and C-H bond functionalization by means of long-distance 1,n-radical migration (n = 4, 5, 6) events. Its advent brings our chemical community a new platform to deal with the challenging migration transformations and thus complements the existing ionic-type migration protocols. In this review, the recent achievements in distal radical migration triggered C-C and C-H bond functionalization are summarized.

Year: 2018 PMID： 29177314 DOI： 10.1039/c7cs00507e

Source DB: PubMed Journal: Chem Soc Rev ISSN： 0306-0012 Impact factor: 54.564

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Cited

15 in total

1. Development of an Imine Chaperone for Selective C-H Functionalization of Alcohols via Radical Relay.

Authors: Kohki M Nakafuku; Raymond K Twumasi; Avassaya Vanitcha; Ethan A Wappes; Kayambu Namitharan; Mathieu Bekkaye; David A Nagib
Journal: J Org Chem Date: 2019-09-12 Impact factor: 4.354

2. Photocatalytic Radical Aroylation of Unactivated Alkenes: Pathway to β-Functionalized 1,4-, 1,6-, and 1,7-Diketones.

Authors: Satavisha Sarkar; Arghya Banerjee; Wang Yao; Eric V Patterson; Ming-Yu Ngai
Journal: ACS Catal Date: 2019-10-17 Impact factor: 13.084

3. Copper-catalyzed enantioselective synthesis of bridged bicyclic ketals from 1,1-disubstituted-4-methylene-1,6-hexanediols and related alkenols.

Authors: Ameya S Burde; Shuklendu D Karyakarte; Eric D Sylvester; Sherry R Chemler
Journal: Chem Commun (Camb) Date: 2021-01-05 Impact factor: 6.222

Distal radical migration strategy: an emerging synthetic means.

1. Development of an Imine Chaperone for Selective C-H Functionalization of Alcohols via Radical Relay.

2. Photocatalytic Radical Aroylation of Unactivated Alkenes: Pathway to β-Functionalized 1,4-, 1,6-, and 1,7-Diketones.

3. Copper-catalyzed enantioselective synthesis of bridged bicyclic ketals from 1,1-disubstituted-4-methylene-1,6-hexanediols and related alkenols.

4. Radical cascade synthesis of azoles via tandem hydrogen atom transfer.

5. Remote C-H functionalization using radical translocating arylating groups.

6. A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes.

7. Pd-catalyzed site-selective C(sp²)-H radical acylation of phenylalanine containing peptides with aldehydes.

8. Radical Aryl Migration from Boron to Carbon.

9. Phosphite mediated asymmetric N to C migration for the synthesis of chiral heterocycles from primary amines.

10. Base-Promoted C-C Bond Activation Enables Radical Allylation with Homoallylic Alcohols.