A highly regio- and stereoselective synthesis of β-haloalkenyl sulfides using commercially available ketones and sulfonyl hydrazides as starting materials has been developed. This protocol obviates the need for alkynes and traditional sulfenylating agents and therefore opens up a new door to construct β-iodoalkenyl sulfides in a highly simple manner. This study reveals that ketones could be used as vinyl iodide precursors in organic synthesis.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.8b00511 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Copper-Catalyzed Radical Sulfonylation: Divergent Construction of C(sp)-Sulfonyl Bonds with Sulfonylhydrazones.
J Org Chem
November 2024
College of Pharmacy, National & Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, IATTI, Chongqing University of Arts and Sciences, Chongqing 402160, China.
Article Synopsis
Application of Chlorosulfonyl Isocyanate (CSI) in the Synthesis of Fused Tetracyclic Ketone Ring Systems.
J Org Chem
November 2024
Department of Chemistry and Biochemistry, Baylor University, One Bear Place #97348, Waco, Texas 76798-7348, United States.
Chlorosulfonyl isocyanate (CSI) is a complex reagent capable of facilitating numerous synthetic transformations, including lactam/lactone formation, sulfonylation, Friedel-Crafts-type acylations, and cycloadditions. Annulation reactions to form nitrogen-, oxygen-, and sulfur-bearing heterocycles have been observed with CSI; however, the application of CSI toward the generation of fused cyclic ketone ring systems has not been previously reported. A serendipitous discovery of the pertinence of CSI occurred during a structure-activity relationship campaign around our established lead benzosuberene-based molecule that functions as a potent inhibitor of tubulin polymerization.
View Article and Find Full Text PDFPhotoredox-Catalyzed Phosphine-Mediated Successive Deoxygenation of Sulfonyl Oxime Salts Enables -Markovnikov Hydrothiolation of Alkenes.
Org Lett
September 2024
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
Stable and easy-to-handle sodium salts of sulfonyl oximes were first identified to proceed via visible-light-driven phophine-mediated successive deoxygenation to realize the -Markovnikov hydrothiolation of alkenes, which could serve as an odorless sulfur source. Mechanistic studies revealed that the key thiyl radical intermediate could be generated from the sulfonyl oxime anion via a phosphine-mediated fragmentation and a sequential deoxygenation process. Notably, a wide range of alkenes, including acrylamides, acrylates, vinyl ketones, vinyl sulfones, and acrylonitriles, are competent substrates for this protocol, which is highly beneficial for the construction of structurally diversified organosulfur compounds.
View Article and Find Full Text PDFCatalytic enantioselective [3+2] and [4+2]-annulation of cyclic -sulfonyl ketimines with γ- or δ-hydroxy-α,β-unsaturated ketones.
Chem Commun (Camb)
July 2024
Department of Chemistry, College of Natural Science, Kyonggi University, 154-42, Gwanggyosan-ro, Yeongtong-gu, Suwon, 16227, Republic of Korea.
A highly efficient asymmetric [3+2] and [4+2]-annulation of cyclic -sulfonyl ketimines with γ- or δ-hydroxy-α,β-unsaturated ketones has been developed. This innovative reaction employs an organocatalytic approach, utilizing a hydrogen-bonding bifunctional squaramide-based catalyst. The process enables precise synthesis of chiral polyheterotricyclic oxazolidines and 1,3-oxazinane derivatives, revealing intricate structures with incorporated chiral quaternary centers.
View Article and Find Full Text PDFUnlocking Enantioselectivity: Synergy of 2-Pyridone and Chiral Amino Acids in Pd-Catalyzed β-C(sp)-H Transformations.
J Org Chem
July 2024
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & B Raja S C Mullick Road, Kolkata 700032, India.
Enantioselective C(sp)-H activation has garnered significant attention in synthetic and computational chemistry. Chiral transient directing groups (TDGs) hold promise for enabling Pd(II)-catalyzed enantioselective C(sp)-H functionalization. Despite the interest in this strategy, it presents a challenge because the stereogenic center on the chiral TDG is frequently distant from the C-H bond, leading to a mixture of functionalized products.
View Article and Find Full Text PDFWant 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!