Desulfonylative Transformations of Sulfones by Transition-Metal Catalysis, Photocatalysis, and Organocatalysis

被引：84

作者：

Nambo, Masakazu ^{[1
]}

Maekawa, Yuuki ^{[1
,2
]}

Crudden, Cathleen M. ^{[1
,2
]}

机构：

[1] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Nagoya, Aichi 4648602, Japan

[2] Queens Univ, Dept Chem, Kingston, ON K7L 4V1, Canada

来源：

ACS CATALYSIS | 2022年 / 12卷 / 05期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

sulfone; catalysis; C-SO2 bond activation; cross-coupling; radical functionalization; CROSS-COUPLING REACTIONS; GRIGNARD-REAGENTS; ALLYLIC ALKYLATION; BOND ACTIVATION; C-O; ORGANOMETALLIC REAGENTS; FLUORINATED SULFONES; PHOTOREDOX CATALYSIS; OXIDATIVE ADDITION; QUINONE METHIDES;

D O I：

10.1021/acscatal.1c05608

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Sulfones are common, readily available reagents that have recently attracted attention as versatile reagents for cross-coupling reactions. This Review summarizes advances in desulfonylative transformations of sulfones affected by molecular catalysis, including transition-metal catalysts, photocatalysts, and organocatalysts. In addition to catalyst choice, the design of the sulfonyl group is a critical factor to control reactivity. The concepts presented herein will provide new strategies to construct diverse molecules with high efficiency and modularity.

引用

页码：3013 / 3032

页数：20

共 140 条

[1] 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

[2] Ligand selectivity by seeking hydrophobicity in thyroid hormone receptor [J].

Borngraeber, S ;

Budny, MJ ;

Chiellini, G ;

Cunha-Lima, ST ;

Togashi, M ;

Webb, P ;

Baxter, JD ;

Scanlan, TS ;

Fletterick, RJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2003, 100 (26) :15358-15363

[3] SYNTHESIS USING SULFONES .24. STEREOSELECTIVE SYNTHESIS OF OLEFINS BY HYDROGENOLYSIS OF VINYLSULFONES [J].

BREMNER, J ;

JULIA, M ;

LAUNAY, M ;

STACINO, JP .

TETRAHEDRON LETTERS, 1982, 23 (32) :3265-3266

[4] Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future [J].

Campeau, Louis-Charles ;

Hazari, Nilay .

ORGANOMETALLICS, 2019, 38 (01) :3-35

[5] Rhodium-Catalyzed Addition of Boronic Acids to Vinylogous Imines Generated in situ from Sulfonylindoles [J].

Cao, Liang-Liang ;

Ye, Zhi-Shi ;

Jiang, Guo-Fang ;

Zhou, Yong-Gui .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (18) :3352-3356

[6] Radical Allylation with α-Branched Allyl Sulfones [J].

Charrier, Nicolas ;

Zard, Samir Z. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (49) :9443-9446

[7] 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

[8] C-C and C-X coupling reactions of unactivated alkyl electrophiles using copper catalysis [J].

Cheng, Li-Jie ;

Mankad, Neal P. .

CHEMICAL SOCIETY REVIEWS, 2020, 49 (22) :8036-8064

[9] Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds [J].

Cherney, Alan H. ;

Kadunce, Nathaniel T. ;

Reisman, Sarah E. .

CHEMICAL REVIEWS, 2015, 115 (17) :9587-9652

[10] Transition metal-catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry [J].

Choi, Junwon ;

Fu, Gregory C. .

SCIENCE, 2017, 356 (6334)

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