Fluorosulfonamide-Directed Heteroarylation of Aliphatic C(sp3)-H Bonds

被引：5

作者：

Pinter, Emily N. ^{[1
]}

Sheldon, Zachary S. ^{[1
]}

Modak, Atanu ^{[1
]}

Cook, Silas P. ^{[1
]}

机构：

[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 07期

基金：

美国国家卫生研究院;

关键词：

C(SP(3))-H HETEROARYLATION; HETEROCYCLIC CHEMISTRY; REMOTE; FUNCTIONALIZATION; FLUORINATION; ALKYLATION;

D O I：

10.1021/acs.joc.2c02461

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we describe a formal dehydrogenative cross coupling of heterocycles with unactivated aliphatic amines. The resulting transformation enables the direct alkylation of common heterocycles by merging N-F-directed 1,5-HAT with Minisci chemistry, leading to predictable site selectivity. The reaction provides a direct route for the transformation of simple alkyl amines to value-added products under mild reaction conditions, making this an attractive option for C(sp3)-H heteroarylation.

引用

收藏

页码：4757 / 4760

页数：4

相关论文

共 33 条

[1] Copper-Catalyzed N-F Bond Activation for Uniform Intramolecular C-H Amination Yielding Pyrrolidines and Piperidines [J].

Bafaluy, Daniel ;

Maria Munoz-Molina, Jose ;

Funes-Ardoiz, Ignacio ;

Herold, Sebastian ;

de Aguirre, Adiran J. ;

Zhang, Hongwei ;

Maseras, Feliu ;

Belderrain, Tomas R. ;

Perez, Pedro J. ;

Muniz, Kilian .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (26) :8912-8916

[2] Catalyst-Controlled 1,2-and 1,1-Arylboration of -Alkyl Alkenyl Arenes [J].

Bergmann, Allison M. ;

Dorn, Stanna K. ;

Smith, Kevin B. ;

Logan, Kaitlyn M. ;

Brown, M. Kevin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (06) :1719-1723

[3] Site-selective remote C(sp3)-H heteroarylation of amides via organic photoredox catalysis [J].

Chen, Hui ;

Fan, Wenjing ;

Yuan, Xiang-Ai ;

Yu, Shouyun .

NATURE COMMUNICATIONS, 2019, 10 (1)

[4] Late-Stage Functionalization of Biologically Active Heterocycles Through Photoredox Catalysis [J].

DiRocco, Daniel A. ;

Dykstra, Kevin ;

Krska, Shane ;

Vachal, Petr ;

Conway, Donald V. ;

Tudge, Matthew .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (19) :4802-4806

[5] Enantioselective Organocatalytic Synthesis of Arylglycines via Friedel-Crafts Alkylation of Arenes with a Glyoxylate Imine [J].

Enders, Dieter ;

Seppelt, Matthias ;

Beck, Tobias .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (09) :1413-1418

[6] The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].

Girard, Simon A. ;

Knauber, Thomas ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100

[7] Iron-Catalyzed, Fluoroamide-Directed C-H Fluorination [J].

Groendyke, Brian J. ;

AbuSalim, Deyaa I. ;

Cook, Silas P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (39) :12771-12774

[8] Heterocyclic Surfactants and Their Applications in Cosmetics [J].

Guin, Mridula ;

Roopa, R. A. ;

Jain, Preeti ;

Singh, Nakshatra Bahadur .

CHEMISTRYSELECT, 2022, 7 (08)

[9] Mechanistic Investigations of Cu-Catalyzed Fluorination of Diaryliodonium Salts: Elaborating the CuI/CuIII Manifold in Copper Catalysis [J].

Ichiishi, Naoko ;

Canty, Allan J. ;

Yates, Brian F. ;

Sanford, Melanie S. .

ORGANOMETALLICS, 2014, 33 (19) :5525-5534

[10] Heterocyclic chemistry in crop protection [J].

Lamberth, Clemens .

PEST MANAGEMENT SCIENCE, 2013, 69 (10) :1106-1114

← 1 2 3 4 →