10.1021/jo00348a046
The main content of the study involves the exploration of the synthesis of (Z)-7-alken-1-ols, which are significant as insect sex attractants, particularly pheromones for various moth species. The researchers utilized organoboranes to achieve a general, one-pot, and stereospecific synthesis of these compounds. The process began with the monohydroboration of 1-alkynes with borepane to produce trans-1-alkenylborepanes. Subsequent treatment of these compounds with iodine in the presence of a base led to a migration of the cycloalkyl chain from boron to the adjacent carbon, forming intermediates with an eight-membered borocane moiety. These intermediates then underwent rapid deiodoboronation to yield (Z)-7-alken-1-boronate esters, which upon oxidation resulted in the desired (Z)-7-alken-1-ols. This method offers a convenient route for the synthesis of specific pheromones, such as (Z)-7-dodecen-1-ol, (2)-7-dodecen-1-yl acetate, and (Z)-7-tetradecen-1-yl acetate, which are crucial for pest control in agriculture.
10.1021/jo102060j
The study presents an efficient method for synthesizing iodoisoquinoline-fused benzimidazole derivatives, which are significant for their potential biological activities such as anti-HIV-1, anticancer, antimicrobial, and antifungal properties. The researchers developed a tandem cyclization strategy using CuI/I2 to promote the electrophilic tandem cyclization of 2-ethynylbenzaldehydes with ortho-benzenediamines. This approach led to the formation of the desired iodoisoquinoline-fused benzimidazoles in moderate to good yields. The study also explored the scope of the reaction with various substrates and demonstrated the potential of the synthesized products for further functionalization through cross-coupling reactions, highlighting the importance of this method for drug discovery and the development of heterocyclic compounds with diverse biological activities.
10.1039/b101074n
The research focuses on the development of solid-phase tandem radical addition-cyclisation reactions of oxime ethers connected with α,β-unsaturated carbonyl groups. The purpose of this study was to effectively form azacycles or chiral oxacycles through C-C bond-forming reactions on a solid support under mild conditions. The researchers used triethylborane as a radical initiator, which demonstrated potential for inducing intermolecular and intramolecular radical reactions on solid support. Key chemicals involved in the process included oxime ethers, a,β-unsaturated carbonyl groups, iodine atom-transfer reagents, and various radical precursors such as cyclohexyl, cyclopentyl, and sec-butyl iodides.
10.1007/BF00912612
The research explores the synthesis and properties of N,N-diiodocarboxamides, a novel class of compounds. The study aims to prepare and characterize these compounds by reacting N,N-dibromocarboxamides with iodine, resulting in the formation of various N,N-diiodocarboxamides such as HCONI2, CH3CONI2, and C6H5CONI2. The research concludes that these compounds exhibit high thermal stability in the solid state but are highly unstable in solution, decomposing to iodine and acyl nitrene. The compounds' low solubility and spectroscopic properties suggest a polymeric structure. The study highlights the significant differences between N,N-diiodocarboxamides and their dibromo analogs, particularly in terms of solubility, stability, and reactivity. The key chemicals used in the research include N,N-dibromocarboxamides, iodine, and various solvents such as carbon tetrachloride (CCl4) and 1,2-dichloroethane.
10.1021/ic2009539
The research investigates the electronic perturbations of iron dipyrrinato complexes through ligand β-halogenation and meso-fluoroarylation. The purpose is to systematically explore how peripheral ligand variations affect the chemistry of transition-metal dipyrrinato complexes, which have potential applications in areas like metal-organic frameworks, fluorescence labeling, and C-H activation chemistry. The researchers synthesized a series of nine dipyrrins with different substituents at the pyrrole backbone (β positions) and the bridgehead methine (meso position), and their FeII complexes. Key chemicals used include pyrrole, various aromatic aldehydes or acetals, DDQ for oxidation, and halogenating agents like N-chlorosuccinimide, N-bromosuccinimide, and iodine. The study found that these ligand modifications caused shifts in electronic absorption maxima, significant changes in electrochemical redox potentials, and notable variations in the FeIII/II redox potential, absorption maxima, and 57Fe M?ssbauer quadrupole splitting of the iron complexes. The results demonstrate that peripheral variation of the dipyrrinato ligand scaffold can systematically alter the chemical and physical properties of iron dipyrrinato complexes.