Continuous Flow as Enabling Technology: Synthesis of Heteroaromatic Sulfinates as Bench Stable Cross-Coupling Partners

被引：8

作者：

Lima, Fabio ^{[1
,2
]}

Andre, Jerome ^{[2
]}

Marziale, Alexander ^{[2
]}

Greb, Andreas ^{[1
]}

Glowienke, Susanne ^{[3
]}

Meisenbach, Mark ^{[1
]}

Schenkel, Berthold ^{[1
]}

Martin, Benjamin ^{[1
]}

Sedelmeier, Joerg ^{[1
]}

机构：

[1] Novartis Pharma AG, Chem & Analyt Dev, CH-4056 Basel, Switzerland

[2] Novartis Inst Biomed Res, Global Discovery Chem, CH-4056 Basel, Switzerland

[3] Novartis Pharma AG, Novartis Inst Biomed Res, Preclin Safety, CH-4056 Basel, Switzerland

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 15期

关键词：

BORONIC ACIDS; ORGANOMETALLIC REAGENTS; SULFONYL FLUORIDES; DUAL CATALYSIS; ARYL; CHEMISTRY; DABSO; SULFONAMIDES; SALTS;

D O I：

10.1021/acs.orglett.0c02155

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enabling continuous flow setup for handling of unstable organolithium intermediates and synthesis of heteroaryl sulfinates on a multigram scale is described. The developed continuous flow process allows for the synthesis and simple isolation of heteroaryl sulfinates which are otherwise challenging to access in classical batch mode. The lithium sulfinate salts prepared by this method were shown to be efficient reaction partners in palladium catalyzed C(sp(2))-C(sp(2)) cross-coupling to access medicinally relevant bis-heteroaryl motifs.

引用

页码：6082 / 6085

页数：4

共 50 条

[31] Continuous-Flow Synthesis of Biaryls by Negishi Cross-Coupling of Fluoro-and Trifluoromethyl-Substituted (Hetero) arenes
Roesner, Stefan
Buchwald, Stephen L.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (35) : 10463 - 10467
[32] Synthesis of air-stable monoligated palladium precatalysts and their applications in cross-coupling reactions
Barnett, Kerry L.
Pierce, Hudson
Wang, Jason
Shaughnessy, Kevin H.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[33] Chemoselective cross-coupling of terminal propargylamines with (het)aroyl chlorides: synthesis of β-aminoacetylenic ketones bearing aromatic and heteroaromatic substituents
P. A. Volkov
K. O. Khrapova
I. A. Bidusenko
A. A. Telezhkin
E. Yu. Schmidt
A. I. Albanov
B. A. Trofimov
Russian Chemical Bulletin, 2022, 71 : 1514 - 1518
[34] Chemoselective cross-coupling of terminal propargylamines with (het)aroyl chlorides: synthesis of β-aminoacetylenic ketones bearing aromatic and heteroaromatic substituents
Volkov, P. A.
Khrapova, K. O.
Bidusenko, I. A.
Telezhkin, A. A.
Schmidt, E. Yu
Albanov, A., I
Trofimov, B. A.
RUSSIAN CHEMICAL BULLETIN, 2022, 71 (07) : 1514 - 1518
[35] A CONVENIENT SYNTHESIS OF SUBSTITUTED HETEROAROMATIC-COMPOUNDS VIA THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF ORGANOSILICON COMPOUNDS
HATANAKA, Y
FUKUSHIMA, S
HIYAMA, T
HETEROCYCLES, 1990, 30 (01) : 303 - 306
[36] Synthesis of Cycloalkyl Substituted 7-Azaindoles via Photoredox Nickel Dual Catalytic Cross-Coupling in Batch and Continuous Flow
Palaychuk, Natalie
DeLano, Travis J.
Boyd, Michael J.
Green, Jeremy
Bandarage, Upul K.
ORGANIC LETTERS, 2016, 18 (23) : 6180 - 6183
[37] Packed-Bed Reactors for Continuous-Flow C-N Cross-Coupling
Naber, John R.
Buchwald, Stephen L.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (49) : 9469 - 9474
[38] High Throughput Experimentation and Continuous Flow Validation of Suzuki-Miyaura Cross-Coupling Reactions
Jaman, Zinia
Mufti, Ahmed
Sah, Samyukta
Avramova, Larisa
Thompson, David H.
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (38) : 9546 - 9554
[39] One-Pot Synthesis of Stable NIR Tetracene Diimides via Double Cross-Coupling
Yue, Wan
Gao, Jing
Li, Yan
Jiang, Wei
Di Motta, Simone
Negri, Fabrizia
Wang, Zhaohui
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (45) : 18054 - 18057
[40] Chemoselective Synthesis of Unsymmetrical Internal Alkynes or Vinyl Sulfones via Palladium-Catalyzed Cross-Coupling Reaction of Sodium Sulfinates with Alkynes
Xu, Yanli
Zhao, Jinwu
Tang, Xiaodong
Wu, Wanqing
Jiang, Huanfeng
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (09) : 2029 - 2039

← 1 2 3 4 5 →