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

[21] Electroreductive Cross-Coupling between Aromatic Aldehydes and Chlorosilanes Enabling the Synthesis of α-Silyl Alcohols
Han, Fen
Su, Qian
Li, Yu
Hao, Jianjun
Peng, Yulin
Zhang, Zhengbing
Jing, Linhai
Han, Pan
ORGANIC LETTERS, 2024, 26 (33) : 7037 - 7042
[22] Homogeneous vs immobilized palladium catalysts for continuous flow cross-coupling chemistry
Cantillo, David
Kappe, C. Oliver
CHIMICA OGGI-CHEMISTRY TODAY, 2015, 33 (04) : 6 - 10
[23] Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling in Continuous Flow
Len, Christophe
Bruniaux, Sophie
Delbecq, Frederic
Parmar, Virinder S.
CATALYSTS, 2017, 7 (05):
[24] Continuous flow mechanochemistry: reactive extrusion as an enabling technology in organic synthesis
Bolt, Robert R. A.
Leitch, Jamie A.
Jones, Andrew C.
Nicholson, William, I
Browne, Duncan L.
CHEMICAL SOCIETY REVIEWS, 2022, 51 (11) : 4243 - 4260
[25] Mild and Rapid Pd-Catalyzed Cross-Coupling with Hydrazine in Continuous Flow: Application to the Synthesis of Functionalized Heterocycles
DeAngelis, Andrew
Wang, Dong-Hui
Buchwald, Stephen L.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (12) : 3434 - 3437
[26] The Continuous-Flow Synthesis of Styrenes Using Ethylene in a Palladium-Catalysed Heck Cross-Coupling Reaction
Bourne, Samuel L.
Koos, Peter
O'Brien, Matthew
Martin, Benjamin
Schenkel, Berthold
Baxendale, Ian R.
Ley, Steven V.
SYNLETT, 2011, (18) : 2643 - 2647
[27] Synthesis of air-stable palladium precatalysts and their reactivity in cross-coupling reactions
Welch, Christopher N.
Shaughnessy, Kevin H.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[28] Fukuyama Cross-Coupling Approach to Isoprekinamycin: Discovery of the Highly Active and Bench-Stable Palladium Precatalyst POxAP
Tang, Shuang-Qi
Bricard, Jacques
Schmitt, Martine
Bihel, Frederic
ORGANIC LETTERS, 2019, 21 (03) : 844 - 848
[29] Allenyl Thianthrenium Salt: A Bench-Stable C3 Synthon for Annulation and Cross-Coupling Reactions
Tewari, Srija
Klask, Nicolai
Ritter, Tobias
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (40) : 27282 - 27286
[30] Suzuki-Miyaura Cross-Coupling of Heteroaryl Halides and Arylboronic Acids in Continuous Flow
Noel, Timothy
Musacchio, Andrew J.
ORGANIC LETTERS, 2011, 13 (19) : 5180 - 5183

← 1 2 3 4 5 →