Palladium‐catalyzed Stereoselective Intramolecular Heck Dearomative Silylation of Indoles

Gang Wang ◽  
Mingzhu Wei ◽  
Tianxiang Liu ◽  
Weiwei Jin ◽  
Yonghong Zhang ◽  
2020 ◽  
Vol 7 (19) ◽  
pp. 2938-2943
Yeojin Kim ◽  
Kwang Ho Song ◽  
Sunwoo Lee

Aryl sulfonyl hydrazide reacted with aryl iodide in the presence of CO to give the corresponding S-aryl thioesters.

2020 ◽  
Vol 7 (6) ◽  
pp. 885-889 ◽  
Xinxin Qi ◽  
Zhi-Peng Bao ◽  
Xiao-Feng Wu

A palladium-catalyzed carbonylative transformation of aryl iodides and sulfonyl chlorides to thioesters has been studied.

Synlett ◽  
1991 ◽  
Vol 1991 (09) ◽  
pp. 697-698 ◽  
Tadakatsu Mandai ◽  
Hiroaki Kunitomi ◽  
Kiyoto Higashi ◽  
Mikio Kawada ◽  
Jiro Tsuji

2020 ◽  
Kiron Kumar Ghosh ◽  
Alexander Uttry ◽  
Francesca Ghiringhelli ◽  
Arup Mondal ◽  
Manuel van Gemmeren

We report the ligand enabled C(sp3)–H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael-addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.<br>

2020 ◽  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

2020 ◽  
Jian Cao ◽  
Ernest Armenta ◽  
Lisa Boatner ◽  
Heta Desai ◽  
Neil Chan ◽  

Bioorthogonal chemistry is a mainstay of chemoproteomic sample preparation workflows. While numerous transformations are now available, chemoproteomic studies still rely overwhelmingly on copper-catalyzed azide –alkyne cycloaddition (CuAAC) or 'click' chemistry. Here we demonstrate that gel-based activity-based protein profiling (ABPP) and mass-spectrometry-based chemoproteomic profiling can be conducted using Suzuki–Miyaura cross-coupling. We identify reaction conditions that proceed in complex cell lysates and find that Suzuki –Miyaura cross-coupling and CuAAC yield comparable chemoproteomic coverage. Importantly, Suzuki–Miyaura is also compatible with chemoproteomic target deconvolution, as demonstrated using structurally matched probes tailored to react with the cysteine protease caspase-8. Uniquely enabled by the observed orthogonality of palladium-catalyzed cross-coupling and CuAAC, we combine both reactions to achieve dual protein labeling.

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