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Literature DB >> 25915558

γ,δ,ε-C(sp(3))-H Functionalization through Directed Radical H-Abstraction.

Tao Liu¹, Tian-Sheng Mei¹, Jin-Quan Yu¹.

Abstract

Aliphatic amides are selectively functionalized at the γ- and δ-positions through directed radical 1,5 and 1,6 H-abstractions, respectively. The initially formed γ- or δ-lactams are intercepted by N-iodosuccinimide and trimethylsilyl azide, leading to double and triple C-H functionalizations at the γ-, δ-, and ε-positions. This new reactivity is exploited to convert alkyls into amino alcohols and allylic amines.

Entities: Chemical Species

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Year: 2015 PMID： 25915558 PMCID： PMC4431913 DOI： 10.1021/jacs.5b02065

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

23 in total

1. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors: Dmitry Shabashov; Olafs Daugulis
Journal: J Am Chem Soc Date: 2010-03-24 Impact factor: 15.419

2. Copper-catalyzed intramolecular C(sp³)-H and C(sp²)-H amidation by oxidative cyclization.

Authors: Zhen Wang; Jizhi Ni; Yoichiro Kuninobu; Motomu Kanai
Journal: Angew Chem Int Ed Engl Date: 2014-02-24 Impact factor: 15.336

3. Radical substitution with azide: TMSN3-PhI(OAc)2 as a substitute of IN3.

Authors: Christian Marcus Pedersen; Lavinia Georgeta Marinescu; Mikael Bols
Journal: Org Biomol Chem Date: 2005-01-27 Impact factor: 3.876

4. Intramolecular hydrogen abstraction reaction promoted by alkoxy radicals in carbohydrates. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems.

Authors: Cosme G Francisco; Antonio J Herrera; Ernesto Suárez
Journal: J Org Chem Date: 2002-10-18 Impact factor: 4.354

5. Delta and alpha SP(3) C-H bond oxidation of sulfonamides with PhI(OAc)(2)/I(2) under metal-free conditions.

Authors: Renhua Fan; Dongming Pu; Fengqi Wen; Jie Wu
Journal: J Org Chem Date: 2007-10-11 Impact factor: 4.354

6. Copper-promoted site-selective acyloxylation of unactivated C(sp³)-H bonds.

Authors: Xuesong Wu; Yan Zhao; Haibo Ge
Journal: Chem Asian J Date: 2014-07-24

7. 1,3-Diol synthesis via controlled, radical-mediated C-H functionalization.

Authors: Ke Chen; Jeremy M Richter; Phil S Baran
Journal: J Am Chem Soc Date: 2008-05-16 Impact factor: 15.419

8. Nickel-catalyzed direct arylation of C(sp3)-H bonds in aliphatic amides via bidentate-chelation assistance.

Authors: Yoshinori Aihara; Naoto Chatani
Journal: J Am Chem Soc Date: 2014-01-09 Impact factor: 15.419

9. Guided desaturation of unactivated aliphatics.

Authors: Ana-Florina Voica; Abraham Mendoza; Will R Gutekunst; Jorge Otero Fraga; Phil S Baran
Journal: Nat Chem Date: 2012-07-08 Impact factor: 24.427

10. Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds.

Authors: Ru-Yi Zhu; Jian He; Xiao-Chen Wang; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2014-09-15 Impact factor: 15.419

20 in total

1. General, Mild, and Selective Method for Desaturation of Aliphatic Amines.

Authors: Padon Chuentragool; Marvin Parasram; Yi Shi; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2018-02-07 Impact factor: 15.419

2. Catalytic alkylation of remote C-H bonds enabled by proton-coupled electron transfer.

Authors: Gilbert J Choi; Qilei Zhu; David C Miller; Carol J Gu; Robert R Knowles
Journal: Nature Date: 2016-10-12 Impact factor: 49.962

3. Identifying Amidyl Radicals for Intermolecular C-H Functionalizations.

Authors: Matthew M Tierney; Stefano Crespi; Davide Ravelli; Erik J Alexanian
Journal: J Org Chem Date: 2019-09-06 Impact factor: 4.354

Review 4. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors: John C K Chu; Tomislav Rovis
Journal: Angew Chem Int Ed Engl Date: 2017-12-05 Impact factor: 15.336

10. Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp³ )-H Sites: Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates.

Authors: Maxim Ratushnyy; Marvin Parasram; Yang Wang; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2018-02-06 Impact factor: 15.336

γ,δ,ε-C(sp(3))-H Functionalization through Directed Radical H-Abstraction.

1. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

2. Copper-catalyzed intramolecular C(sp³)-H and C(sp²)-H amidation by oxidative cyclization.

3. Radical substitution with azide: TMSN3-PhI(OAc)2 as a substitute of IN3.

4. Intramolecular hydrogen abstraction reaction promoted by alkoxy radicals in carbohydrates. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems.

5. Delta and alpha SP(3) C-H bond oxidation of sulfonamides with PhI(OAc)(2)/I(2) under metal-free conditions.

6. Copper-promoted site-selective acyloxylation of unactivated C(sp³)-H bonds.

7. 1,3-Diol synthesis via controlled, radical-mediated C-H functionalization.

8. Nickel-catalyzed direct arylation of C(sp3)-H bonds in aliphatic amides via bidentate-chelation assistance.

9. Guided desaturation of unactivated aliphatics.

10. Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds.

1. General, Mild, and Selective Method for Desaturation of Aliphatic Amines.

2. Catalytic alkylation of remote C-H bonds enabled by proton-coupled electron transfer.

3. Identifying Amidyl Radicals for Intermolecular C-H Functionalizations.

Review 4. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

5. Sulfamate Esters Guide C(3)-Selective Xanthylation of Alkanes.

6. δ-C-H Mono- and Dihalogenation of Alcohols.

7. Remote C-H Functionalization via Selective Hydrogen Atom Transfer.

8. Vicinal, Double C-H Functionalization of Alcohols via an Imidate Radical-Polar Crossover Cascade.

9. Triiodide-Mediated δ-Amination of Secondary C-H Bonds.

10. Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp³ )-H Sites: Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates.

Review 4. Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Review 4. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.