Pd-catalyzed Suzuki-type cross-coupling of 2-pyridyl carbamoyl fluorides

被引：2

作者：

Jabbarpoor, Maryam ^{[1
]}

LeBlanc, Jesse ^{[1
]}

Chen, Zichuan ^{[1
]}

Cadwallader, Dusty ^{[1
]}

Le, Christine M. ^{[1
]}

机构：

[1] York Univ, Dept Chem, 4700 Keele St, Toronto, ON M3J 1P3, Canada

来源：

CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 66期

基金：

加拿大自然科学与工程研究理事会;

关键词：

OXIDATIVE AMIDATION; DERIVATIVES; ACTIVATION; OXINDOLES; DESIGN; AMIDES;

D O I：

10.1039/d4cc02431a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe a palladium-catalyzed Suzuki-type cross-coupling reaction of 2-pyridyl carbamoyl fluorides with boronic acids, which provides entry to medicinally relevant pyridyl amides. Mechanistic studies, including the synthesis and reactivity of carbamoyl Pd-F complexes, reveal the importance of both the fluoride electrophile and nitrogen directing group for aiding reactivity. A directing group strategy enables the Pd-catalyzed Suzuki-type cross-coupling of carbamoyl fluorides with boronic acids to yield medicinally relevant pyridyl amides.

引用

页码：8700 / 8703

页数：4

共 34 条

[1] DIRECT ACYLAMINATION OF PYRIDINE 1-OXIDES [J].

ABRAMOVI.RA ;

SINGER, GM .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (13) :1795-1802

[2] A Scalable Route for the Regio- and Enantioselective Preparation of a Tetrazole Prodrug: Application to the Multi-Gram-Scale Synthesis of a PCSK9 Inhibitor [J].

Akin, Anne ;

Barrila, Mark T. ;

Brandt, Thomas A. ;

Dechert-Schmitt, Anne-Marie R. ;

Dube, Pascal ;

Ford, David D. ;

Kamlet, Adam S. ;

Limberakis, Chris ;

Pearsall, Andrew ;

Piotrowski, David W. ;

Quinn, Brian ;

Rothstein, Sarah ;

Salan, Jerry ;

Wei, Liuqing ;

Xiao, Jun .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2017, 21 (12) :1990-2000

[3] A rare example of the in situ formation of palladium nanoparticles: The emergence of catalytically active palladium nanoparticles from Pd (II) phosphine complexes in the Suzuki-Miyaura coupling reaction [J].

Altan, Orhan .

APPLIED ORGANOMETALLIC CHEMISTRY, 2022, 36 (06)

[4] Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone? [J].

Brow, Dean G. ;

Bostrom, Jonas .

JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (10) :4443-4458

[5] Fluoride-Catalyzed Cross-Coupling of Carbamoyl Fluorides and Alkynylsilanes [J].

Cadwallader, Dusty ;

Shevchuk, Dmytro ;

Tiburcio, Tristan R. ;

Le, Christine M. .

ORGANIC LETTERS, 2023, 25 (40) :7369-7373

[6] Synthesis of Carbamoyl Fluorides Using a Difluorophosgene Surrogate Derived from Difluorocarbene and Pyridine N-Oxides [J].

Cadwallader, Dusty ;

Tiburcio, Tristan R. ;

Cieszynski, George A. ;

Le, Christine M. .

JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (17) :11457-11468

[7] Synthesis of β-Lactams by Palladium(0)-Catalyzed C(sp3)-H Carbamoylation [J].

Dailler, David ;

Rocaboy, Ronan ;

Baudoin, Olivier .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (25) :7218-7222

[8] Triphenylphosphine chalcogenides as efficient ligands for room temperature palladium(II)-catalyzed Suzuki-Miyaura reaction [J].

Das, Pankaj ;

Bora, Utpal ;

Tairai, Archana ;

Sharma, Chandan .

TETRAHEDRON LETTERS, 2010, 51 (11) :1479-1482

[9] Phosphine oxides as stabilizing ligands for the palladium-catalyzed cross-coupling of potassium aryldimethylsilanolates [J].

Denmark, Scott E. ;

Smith, Russell C. ;

Tymonko, Steven A. .

TETRAHEDRON, 2007, 63 (26) :5730-5738

[10] Metal-free oxidative amidation of aldehydes with aminopyridines employing aqueous hydrogen peroxide [J].

Devi, E. Sankari ;

Alanthadka, Anitha ;

Tamilselvi, A. ;

Nagarajan, Subbiah ;

Sridharan, Vellaisamy ;

Maheswari, C. Uma .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (35) :8228-8231

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