Nickel-Catalyzed Desulfonylative Reductive Cross-Coupling of Aryl Sulfones with Aryl Bromides

被引：13

作者：

Huang, Xinmiao ^{[1
,2
]}

Tang, Ling ^{[1
,2
]}

Song, Zhiyong ^{[1
,2
]}

Jiang, Shuangshuang ^{[1
,2
]}

Liu, Xianmao ^{[1
,2
]}

Ma, Ming ^{[1
,2
]}

Chen, Bo ^{[1
,2
]}

Ma, Yuanhong ^{[1
,2
]}

机构：

[1] Hunan Normal Univ, Coll Chem & Chem Engn, Key Lab Phytochemistry R&D Hunan Prov, Key Lab Chem Biol & Tradit Chinese Med Res,Minist, Changsha 410081, Peoples R China

[2] Hunan Normal Univ, Coll Chem & Chem Engn, Key Lab Assembly & Applicat Organ Funct Mol Hunan, Changsha 410081, Peoples R China

来源：

ORGANIC LETTERS | 2023年

基金：

中国国家自然科学基金;

关键词：

SULFIDES; HALIDES; BONDS;

D O I：

10.1021/acs.orglett.3c00185

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, a nickel catalysis system for desulfonylative C(sp(2))-C(sp(2)) reductive cross-coupling reactions of aryl sulfone derivatives with a range of aryl bromides has been established to form diverse biaryl compounds. The complex Ar-Ni(II)-SO(2)CF3 bearing a phosphine ligand through oxidative addition of aryl sulfone to Ni(0) species was isolated and confirmed by an X-ray, which provides solid evidence for the understanding of the C(Ar)-SO2 bond activation and reaction mechanism.

引用

页码：1198 / 1203

页数：6

共 38 条

[1] Multimetallic catalysed cross-coupling of aryl bromides with aryl triflates [J].

Ackerman, Laura K. G. ;

Lovell, Matthew M. ;

Weix, Daniel J. .

NATURE, 2015, 524 (7566) :454-+

[2] Preparation of Quaternary Centers via Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Tertiary Sulfones [J].

Ariki, Zachary T. ;

Maekawa, Yuuki ;

Nambo, Masakazu ;

Crudden, Cathleen M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (01) :78-81

[3] Desulfonative Suzuki-Miyaura Coupling of Sulfonyl Fluorides [J].

Chatelain, Paul ;

Muller, Cyprien ;

Sau, Abhijit ;

Brykczynska, Daria ;

Bahadori, Maryam ;

Rowley, Christopher N. ;

Moran, Joseph .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (48) :25307-25312

[4] Suzuki-Miyaura Coupling of (Hetero)Aryl Sulfones: Complementary Reactivity Enables Iterative Polyaryl Synthesis [J].

Chatelain, Paul ;

Sau, Abhijit ;

Rowley, Christopher N. ;

Moran, Joseph .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (42) :14959-14963

[5] Desulfonylation via Radical Process: Recent Developments in Organic Synthesis [J].

Chu, Xue-Qiang ;

Ge, Danhua ;

Cui, Yan-Ying ;

Shen, Zhi-Liang ;

Li, Chao-Jun .

CHEMICAL REVIEWS, 2021, 121 (20) :12548-12680

[6] Beyond classical sulfone chemistry: metal- and photocatalytic approaches for C-S bond functionalization of sulfones [J].

Corpas, Javier ;

Kim-Lee, Shin-Ho ;

Mauleon, Pablo ;

Arrayas, Ramon Gomez ;

Carretero, Juan C. .

CHEMICAL SOCIETY REVIEWS, 2022, 51 (15) :6774-6823

[7] Photoredox/Nickel Dual-Catalyzed Reductive Cross Coupling of Aryl Halides Using an Organic Reducing Agent [J].

Dewanji, Abhishek ;

Buelow, Raoul F. ;

Rueping, Magnus .

ORGANIC LETTERS, 2020, 22 (04) :1611-1617

[8] Cobalt-Catalyzed C(sp2)-CN Bond Activation: Cross-Electrophile Coupling for Biaryl Formation and Mechanistic Insight [J].

Dorval, Celine ;

Tricoire, Maxime ;

Begouin, Jeanne-Marie ;

Gandon, Vincent ;

Gosmini, Corinne .

ACS CATALYSIS, 2020, 10 (21) :12819-12827

[9] Covalent Enzyme Inhibition through Fluorosulfate Modification of a Noncatalytic Serine Residue [J].

Fadeyi, Olugbeminiyi O. ;

Hoth, Lise R. ;

Choi, Chulho ;

Feng, Xidong ;

Gopalsamy, Ariamala ;

Hett, Erik C. ;

Kyne, Robert E., Jr. ;

Robinson, Ralph P. ;

Jones, Lyn H. .

ACS CHEMICAL BIOLOGY, 2017, 12 (08) :2015-2020

[10] Cross-Coupling of Aryl Trifluoromethyl Sulfones with Arylboronates by Cooperative Palladium/Rhodium Catalysis [J].

Fukuda, Jun-ichi ;

Nogi, Keisuke ;

Yorimitsu, Hideki .

ORGANIC LETTERS, 2019, 21 (22) :8987-8991

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