Palladium-Catalyzed anti-Markovnikov Oxidative Acetalization of Activated Olefins with Iron(III) Sulphate as Benign Reoxidant

2022 ◽  
Author(s):  
Rodney Agustinho Fernandes ◽  
Sandhya Singh Yadav ◽  
Praveen Kumar
Keyword(s):  
Reaction Conditions ◽  
Palladium Catalyzed ◽  
Activated Olefins ◽  
Terminal Olefins

This paper discloses the efficient palladium-catalyzed anti-Markovnikov oxidative acetalization of activated terminal olefins with iron(III) sulfate as benign reoxidant. This methodology depicts mild reaction conditions, high regioselectivity toward anti-Makovnikov products...

Suzuki–Miyaura cross-coupling for chemoproteomic applications

2020 ◽  
Author(s):  
Jian Cao ◽  
Ernest Armenta ◽  
Lisa Boatner ◽  
Heta Desai ◽  
Neil Chan ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Cross Coupling ◽  
Protein Profiling ◽  
Protein Labeling ◽  
Caspase 8 ◽  
Complex Cell ◽  
Bioorthogonal Chemistry ◽  
Reaction Conditions ◽  
Target Deconvolution ◽  
Palladium Catalyzed

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.

Recent Developments in Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles

Synthesis ◽  
2020 ◽  
Author(s):  
Lili Shi ◽  
Junkai Fu ◽  
Shuangqiu Gao ◽  
Le Chang ◽  
Binglin Wang
Keyword(s):  
Heck Reaction ◽  
Alkyl Radicals ◽  
Type Reaction ◽  
The Past ◽  
Alkyl Electrophiles ◽  
Recent Developments ◽  
Palladium Catalyzed ◽  
Initial Work ◽  
Activated Olefins ◽  
Pseudo Halides

AbstractThe Mizoroki–Heck reaction is considered as one of the most ingenious and widely used methods for constructing C–C bonds. This reaction mainly focuses on activated olefins (styrenes, acrylates, or vinyl ethers) and aryl/vinyl (pseudo) halides. In comparison, the studies on unactivated alkenes and alkyl electrophiles are far less due to the low reactivity, poor selectivity, as well as competitive β-H elimination. In the past years, a growing interest has thus been devoted and significant breakthroughs have been achieved in the employment of unactivated alkenes and alkyl electrophiles as the reaction components, and this type of coupling is called as Heck-type or Heck-like reaction, which distinguishes from the traditional Heck reaction. Herein, we give a brief summary on Heck-type reaction between unactivated alkenes and alkyl electrophlies, covering its initial work, recent advancements, and mechanistic discussions.1 Introduction2 Intramolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles2.1 Cobalt-Catalyzed Intramolecular Heck-Type Reaction2.2 Palladium-Catalyzed Intramolecular Heck-Type Reaction2.3 Nickel-Catalyzed Intramolecular Heck-Type Reaction2.4 Photocatalysis and Multimetallic Protocol for Intramolecular Heck-Type Reaction3 Intermolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles3.1 Electrophilic Trifluoromethylating Reagent as Reaction Partners3.2 Alkyl Electrophiles as Reaction Partners4 Oxidative Heck-Type Reaction of Unactivated Alkenes and Alkyl Radicals5 Conclusions and Outlook

ChemInform Abstract: Palladium-Catalyzed Double Arylations of Terminal Olefins in Acetic Acid.

ChemInform ◽  
2012 ◽  
Vol 43 (27) ◽  
pp. no-no
Author(s):  
Daichao Xu ◽  
Chunxin Lu ◽  
Wanzhi Chen
Keyword(s):  
Acetic Acid ◽  
Palladium Catalyzed ◽  
Terminal Olefins

Palladium-Catalyzed Aminoallylation of Activated Olefins with Allylic Halides and Phthalimide

2002 ◽  
Vol 67 (17) ◽  
pp. 5977-5980 ◽  
Author(s):  
Kouichi Aoyagi ◽  
Hiroyuki Nakamura ◽  
Yoshinori Yamamoto
Keyword(s):  
Palladium Catalyzed ◽  
Activated Olefins ◽  
Allylic Halides

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

Visible-Light Photoredox-Catalyzed Cascade Reaction for the Synthesis of Pyrrolo[2,1-a]isoquinoline-Substituted Phosphonates

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 522-529 ◽  
Author(s):  
Deqing Shi ◽  
Lingna Wang ◽  
Tiancong Ma ◽  
Mingming Qiao ◽  
Qiangxian Wu ◽  
...  
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Cascade Reaction ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Oxidative Aromatization ◽  
Activated Olefins ◽  
Catalyzed Oxidation

A visible-light photoredox-catalyzed oxidation/[3+2] cycloaddition/oxidative aromatization cascade reaction of [(3,4-dihydroisoquinolin-2(1H)-yl)methyl]phosphonates and activated olefins or alkynes for the efficient synthesis of potentially biological active pyrrolo[2,1-a]isoquinoline-substituted phosphonates was developed. This transformation features mild reaction conditions (i.e., visible light irradiation, room temperature), molecular oxygen (O2) as a green oxidant, simple ‘one-pot’ operation.

Palladium-catalyzed highly regioselective hydroaminocarbonylation of aromatic alkenes to branched amides

2017 ◽  
Vol 15 (14) ◽  
pp. 2910-2913 ◽  
Author(s):  
Jinping Zhu ◽  
Bao Gao ◽  
Hanmin Huang
Keyword(s):  
Reaction Conditions ◽  
Efficient Catalyst ◽  
Palladium Catalyzed

Pd(t-Bu3P)2 has been successfully identified as an efficient catalyst for the hydroaminocarbonylation of aromatic alkenes to branched amides under relatively mild reaction conditions.

A Palladium-Catalyzed Dehydrogenative Diamination of Terminal Olefins

2008 ◽  
Vol 120 (43) ◽  
pp. 8348-8351 ◽  
Author(s):  
Bin Wang ◽  
Haifeng Du ◽  
Yian Shi
Keyword(s):  
Palladium Catalyzed ◽  
Terminal Olefins
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