Molecular Iodine-Mediated Difunctionalization of Alkenes with Nitriles and Thiols Leading to β-Acetamido Sulfides.

J Org Chem

The Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong China.

Published: March 2016

A direct difunctionalization protocol of alkenes with nitriles and thiols toward β-acetamido sulfide derivatives has been proposed under metal-free synthesis conditions. The present protocol provides the facile and highly efficient synthesis of various β-acetamido sulfides in a scaled-up manner with good to excellent yields simply using inexpensive molecular iodine as a catalyst, DMSO as a mild oxidant, and readily available thiols as thiolating reagents.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.5b02579DOI Listing

Publication Analysis

Top Keywords

alkenes nitriles
8
nitriles thiols
8
β-acetamido sulfides
8
molecular iodine-mediated
4
iodine-mediated difunctionalization
4
difunctionalization alkenes
4
thiols leading
4
leading β-acetamido
4
sulfides direct
4
direct difunctionalization
4

Similar Publications

Background: Diabetes mellitus is associated with morphological and functional impairment of the heart primarily due to lipid toxicity caused by increased fatty acid metabolism. Extracellular signal-regulated protein kinases 1 and 2 (ERK1/2) have been implicated in the metabolism of fatty acids in the liver and skeletal muscles. However, their role in the heart in diabetes remains unclear.

View Article and Find Full Text PDF

Revealing the roles of solar withering and shaking processes on oolong tea manufacturing from transcriptome and volatile profile analysis.

Food Res Int

February 2025

Department of Horticulture and Landscape Architecture, National Taiwan University, Taipei 10617, Taiwan; Center for Biotechnology, National Taiwan University, Taipei 10672, Taiwan. Electronic address:

Solar and indoor withering in the manufacturing process of semi-fermented oolong tea are crucial for aroma formation. While the processes have been established through accumulated experience, the underlying mechanisms remain largely unknown. This study identified pairs of gene and volatile organic compound (VOC) that were significantly correlated and up-regulated during solar withering and the first shaking, including lipoxygenase 8 (LOX8) with 3-hexenyl iso-butyrate, terpene synthase 2 (TPS2) with β-ocimene and linalool, as well as tryptophan synthase β-subunit 2 (TSB2) with indole.

View Article and Find Full Text PDF

Molecular Photoelectrocatalysis for Radical Reactions.

Acc Chem Res

January 2025

State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, and Discipline of Intelligent Instrument and Equipment, Xiamen University, Xiamen 361005, P. R. China.

ConspectusMolecular photoelectrocatalysis, which combines the merits of photocatalysis and organic electrosynthesis, including their green attributes and capacity to offer novel reactivity and selectivity, represents an emerging field in organic chemistry that addresses the growing demands for environmental sustainability and synthetic efficiency. This synergistic approach permits access to a wider range of redox potentials, facilitates redox transformations under gentler electrode potentials, and decreases the use of external harsh redox reagents. Despite these potential advantages, this area did not receive significant attention until 2019, when we and others reported the first examples of modern molecular photoelectrocatalysis.

View Article and Find Full Text PDF

Bacterial contamination is a major public health concern on a global scale. Treatment resistance in bacterial infections is becoming a significant problem that requires solutions. We were interested in obtaining new polymeric functionalized compounds with antibacterial properties.

View Article and Find Full Text PDF

We report a Ni-catalyzed vicinal alkylarylation of unactivated alkenes in γ,δ- and δ,ε-alkenylamines with aryl halides and alkylzinc reagents. The reaction is enabled by amine coordination and can use all primary, secondary, and tertiary amines. The reaction constructs two new C(sp)-C(sp) and C(sp)-C(sp) bonds and produces δ- and ε-arylamines with C(sp)-branching at the γ- and δ-positions.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!