Electroreductive Nickel-Catalyzed Allylation of Aryl Chlorides

被引：9

作者：

Fu, Xin ^{[1
]}

Ran, Tingting ^{[1
]}

Zhou, Yu ^{[1
]}

Liu, Jie ^{[2
,3
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, Changsha 410082, Peoples R China

[2] Hunan Univ, Coll Chem & Chem Engn, Changsha 410082, Peoples R China

[3] Hunan Univ, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 09期

关键词：

CROSS-COUPLING REACTIONS; ELECTROCHEMICAL ALLYLATION; ALLYLIC SUBSTITUTION; ALKYL-HALIDES; METAL; LIGHT; DERIVATIVES; PHOTOREDOX; IODIDES;

D O I：

10.1021/acs.joc.2c02926

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report a facile and efficient allylation via electrochemical promoted Ni-catalyzed reductive carbon-carbon bond formation. Readily available (hetero)aryl chlorides with a variety of allylic sulfones are used as electrophiles in this electroreductive coupling. This Nicatalyzed modular approach displays generally good functional group tolerance and broad substrate scope. This reaction allows a series of allylic compounds to be created including several structurally complex natural products and pharmaceutical motifs.

引用

页码：6132 / 6139

页数：8

共 65 条

[11] Visible Light Promoted Metal- and Photocatalyst-Free Synthesis of Allylarenes [J].

Dossena, Alessandro ;

Sampaolesi, Susanna ;

Palmieri, Alessandro ;

Protti, Stefano ;

Fagnoni, Maurizio .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19) :10687-10692

[12] Nickel-catalyzed direct electrochemical cross-coupling between aryl halides and activated alkyl halides [J].

Durandetti, M ;

Nedelec, JY ;

Perichon, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1748-1755

[13] Iron-catalyzed electrochemical allylation of carbonyl compounds by allylic acetates [J].

Durandetti, M ;

Meignein, C ;

Périchon, J .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08) :3121-3124

[14] Asymmetric induction in the electrochemical cross-coupling of aryl halides with alpha-chloropropionic acid derivatives catalyzed by nickel complexes [J].

Durandetti, M ;

Perichon, J ;

Nedelec, JY .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :7914-7915

[15] Cross-Electrophile Coupling: Principles of Reactivity and Selectivity [J].

Everson, Daniel A. ;

Weix, Daniel J. .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11) :4793-4798

[16] Regioselective Cross-Coupling of Allylboronic Acid Pinacol Ester Derivatives with Aryl Halides via Pd-PEPPSI-IPent [J].

Farmer, Jennifer L. ;

Hunter, Howard N. ;

Organ, Michael G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) :17470-17473

[17] Nickel-Catalyzed Reductive Allyl-Aryl Cross-Electrophile Coupling via Allylic C-F Bond Activation [J].

Fujita, Takeshi ;

Kobayashi, Yutaro ;

Takahashi, Ikko ;

Morioka, Ryutaro ;

Ichitsuka, Tomohiro ;

Ichikawa, Junji .

CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (02)

[18] Nickel-Catalyzed Allylic Substitution Reactions: An Evolving Alternative [J].

Ghorai, Debasish ;

Cristofol, Alex ;

Kleij, Arjan W. .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2022, 2022 (02)

[19] Cobalt-catalyzed direct electrochemical cross-coupling between aryl or heteroaryl halides and allylic acetates or carbonates [J].

Gomes, P ;

Gosmini, C ;

Périchon, J .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :1142-1145

[20] TRANSFORMATIONS OF CHLOROARENES, CATALYZED BY TRANSITION-METAL COMPLEXES [J].

GRUSHIN, VV ;

ALPER, H .

CHEMICAL REVIEWS, 1994, 94 (04) :1047-1062

← 1 2 3 4 5 6 7 →