Cyano migration-mediated radical-polar crossover cyclopropanation

被引：0

作者：

Ziqiang Wang ^{[1
,2
]}

Yasu Chen ^{[2
]}

Jie Li ^{[1
]}

Chen Zhu ^{[1
,2
]}

机构：

[1] Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science,Soochow University

[2] Frontiers Science Center for Transformative Molecules, Zhangjiang Institute for Advanced Study and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University

来源：

Science China(Chemistry) | 2025年 / 68卷 / 01期

关键词：

D O I：

暂无

中图分类号：

O621.251 [];

学科分类号：

070303 ; 081704 ;

摘要：

We report a novel cyano migration-mediated radical-polar crossover process, whereby both the sulfonylcyanation of aliphatic alkenes and the formation of cyclopropanes are concurrently achieved. This transformation yields a diverse array of multisubstituted cyclopropanes under mild photocatalytic conditions. Mechanistic studies elucidate that the reaction proceeds via intramolecular nucleophilic substitution, leading to the formation of the cyclopropane derivatives.

引用

页码：241 / 248

页数：8

共 50 条

[21] Photocatalyzed Azidofunctionalization of Alkenes via Radical-Polar Crossover [J].

Palamini, Pierre ;

Schoepfer, Alexandre A. ;

Waser, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (08)

[22] Radical-polar crossover reactions of vinylboron ate complexes [J].

Kischkewitz, Marvin ;

Okamoto, Kazuhiro ;

Mueck-Lichtenfeld, Christian ;

Studer, Armido .

SCIENCE, 2017, 355 (6328) :936-+

[23] Hydroarylation of Arenes via Reductive Radical-Polar Crossover [J].

Flynn, Autumn R. ;

McDaniel, Kelly A. ;

Hughes, Meredith E. ;

Vogt, David B. ;

Jui, Nathan T. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (20) :9163-9168

[24] A Radical-Polar Crossover Annulation To Access Terpenoid Motifs [J].

Thomas, William P. ;

Schatz, Devon J. ;

George, David T. ;

Pronin, Sergey V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (31) :12246-12250

[25] Stereocontrolled synthesis of complex polycycles using tetrathiafulvalene mediated radical-polar crossover reactions [J].

Fletcher, RJ ;

Hibbs, DE ;

Hursthouse, M ;

Lampard, C ;

Murphy, JA ;

Roome, SJ .

CHEMICAL COMMUNICATIONS, 1996, (06) :739-740

[26] Synthesis of the acutumine spirocycle via a radical-polar crossover reaction [J].

Li, Fang ;

Castle, Steven L. .

ORGANIC LETTERS, 2007, 9 (20) :4033-4036

[27] Radical-Polar Crossover Annulation: A Platform for Accessing Polycyclic Cyclopropanes [J].

Milligan, John A. ;

Burns, Kevin L. ;

Le, Anthony, V ;

Polites, Viktor C. ;

Wang, Zheng-Jun ;

Molander, Gary A. ;

Kelly, Christopher B. .

ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (01) :242-247

[28] Visible Light Assisted Radical-Polar/Polar-Radical Crossover Reactions in Organic Synthesis [J].

Sharma, Shivani ;

Singh, Jitender ;

Sharma, Anuj .

ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (13) :3146-3169

[29] Reductive radical-polar crossover: traditional electrophiles in modern radical reactions [J].

Pitzer, Lena ;

Schwarz, J. Luca ;

Glorius, Frank .

CHEMICAL SCIENCE, 2019, 10 (36) :8285-8291

[30] Radical-polar crossover reactions with polymer-supported tetrathiafulvalene [J].

Patro, B ;

Merrett, M ;

Murphy, JA ;

Sherrington, DC ;

Morrison, MGJT .

TETRAHEDRON LETTERS, 1999, 40 (44) :7857-7860

← 1 2 3 4 5 →