Palladium-Catalyzed Unimolecular Fragment Coupling of N -Allylamides Bearing a Tethered Nucleophile with the Translocation of an Amide Group

被引：5

作者：

Shimazumi, Ryoma ^{[1
]}

Kodama, Takuya ^{[1
,2
]}

Tobisu, Mamoru ^{[1
,2
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Inst Open & Transdisciplinary Res Initiat ICS OTRI, Innovat Catalysis Sci Div, Suita, Osaka 5650871, Japan

来源：

SYNTHESIS-STUTTGART | 2023年 / 56卷 / 01期

基金：

日本学术振兴会; 日本科学技术振兴机构;

关键词：

palladium catalyst; C-N bond activation; amides; isocyanates; elimination; rearrangement; ALKENES; BONDS;

D O I：

10.1055/a-2022-1905

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed reaction of N-allylamides bearing a tethered nucleophile results in the extrusion of an amide moiety in the form of an isocyanate, with its subsequent capture by the pendant nucleophile. This reaction involves the net catalytic transposition of an amide group.

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收藏

页码：134 / 142

页数：9

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[1] Skeletal Editing of Pyrimidines to Pyrazoles by Formal Carbon Deletion [J].

Bartholomew, G. Logan ;

Carpaneto, Filippo ;

Sarpong, Richmond .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (48) :22309-22315

[2] Late-Stage Functionalization [J].

Boergel, Jonas ;

Ritter, Tobias .

CHEM, 2020, 6 (08) :1877-1887

[3] Deoxygenation of Ethers To Form Carbon-Carbon Bonds via Nickel Catalysis [J].

Cao, Zhi-Chao ;

Shi, Zhang-Jie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (19) :6546-6549

[4] The medicinal chemist's toolbox for late stage functionalization of drug-like molecules [J].

Cernak, Tim ;

Dykstra, Kevin D. ;

Tyagarajan, Sriram ;

Vachal, Petr ;

Krska, Shane W. .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) :546-576

[5] Catalytic Carbochlorocarbonylation of Unsaturated Hydrocarbons via C-COCl Bond Cleavage** [J].

Denton, Elliott H. ;

Lee, Yong Ho ;

Roediger, Sven ;

Boehm, Philip ;

Fellert, Maximilian ;

Morandi, Bill .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (43) :23435-23443

[6] Domino Decarboxylation-CO2Fixation - a Route toward Cyclic Carbonates and Oxazolidinones (Microreview) [J].

Feng, Huangdi .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (05) :506-508

[7] Peptide Carbocycles: From -SS- to -CC- via a Late-Stage "Snip- and-Stitch" [J].

Gary, Samuel ;

Bloom, Steven .

ACS CENTRAL SCIENCE, 2022, 8 (11) :1537-1547

[8] Unified Access to Pyrimidines and Quinazolines Enabled by N-N Cleaving Carbon Atom Insertion [J].

Hyland, Ethan E. ;

Kelly, Patrick Q. ;

McKillop, Alexander M. ;

Dherange, Balu D. ;

Levin, Mark D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (42) :19258-19264

[9] Nickel-Catalyzed Addition of C-C Bonds of Amides to Strained Alkenes: The 1,2-Carboaminocarbonylation Reaction [J].

Ito, Yuri ;

Nakatani, Syun ;

Shiraki, Ryota ;

Kodama, Takuya ;

Tobisu, Mamoru .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (02) :662-666

[10] Single-atom logic for heterocycle editing [J].

Jurczyk, Justin ;

Woo, Jisoo ;

Kim, Sojung F. ;

Dherange, Balu D. ;

Sarpong, Richmond ;

Levin, Mark D. .

NATURE SYNTHESIS, 2022, 1 (05) :352-364

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