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On the Hydrostannylation of Aryl Propargylic Alcohols and Their Derivatives: Remarkable Differences in Both Regio‐ and Stereoselectivity in Radical‐ and Nonradical‐Mediated Transformations 下载免费PDF全文
Dr. Martins S. Oderinde Dr. Robert D. J. Froese Prof. Michael G. Organ 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(28):8579-8583
Herein, we describe a highly regio‐ and stereoselective radical‐mediated and molecular‐oxygen (O2)‐dependent hydrostannylation of phenyl propargylic alcohols and their derivatives. There is a significant steric effect on the stereoselectivity of the tin‐radical addition. Further, the uncatalyzed regio‐ and stereoselective hydrostannylation of aryl propargylic alcohols with nBu3SnH and Ph3SnH is also described and occurs with near titration kinetics. Although the uncatalyzed addition with nBu3SnH gave a remarkable γ‐regioselectivity irrespective of the electronic nature of the aryl moiety, addition with Ph3SnH appears to be driven by the electronic nature of the aryl alkynes. 相似文献
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Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross‐Coupling of Primary Aryl Amines with Aryl Halides 下载免费PDF全文
Dr. Martins S. Oderinde Natalie H. Jones Antoine Juneau Prof. Mathieu Frenette Dr. Brian Aquila Sharon Tentarelli Dr. Daniel W. Robbins Dr. Jeffrey W. Johannes 《Angewandte Chemie (International ed. in English)》2016,55(42):13219-13223
A visible‐light‐promoted iridium photoredox and nickel dual‐catalyzed cross‐coupling procedure for the formation C?N bonds has been developed. With this method, various aryl amines were chemoselectively cross‐coupled with electronically and sterically diverse aryl iodides and bromides to forge the corresponding C?N bonds, which are of high interest to the pharmaceutical industries. Aryl iodides were found to be a more efficient electrophilic coupling partner. The coupling reactions were carried out at room temperature without the rigorous exclusion of molecular oxygen, thus making this newly developed Ir‐photoredox/Ni dual‐catalyzed procedure very mild and operationally simple. 相似文献
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Ethan R. Sauv Don M. Mayder Saeid Kamal Martins S. Oderinde Zachary M. Hudson 《Chemical science》2022,13(8):2296
Energy transfer (EnT) is a fundamental activation process in visible-light-promoted photocycloaddition reactions. This work describes the performance of imidazoacridine-based TADF materials for visible-light mediated triplet–triplet EnT photocatalysis. The TADF material ACR-IMAC has been discovered as an inexpensive, high-performance organic alternative to the commonly used metal-based photosensitizers for visible-light EnT photocatalysis. The efficiency of ACR-IMAC as a photosensitizer is comparable with Ir-based photosensitizers in both intra- and intermolecular [2 + 2] cycloadditions. ACR-IMAC mediated both dearomative and non-dearomative [2 + 2] cycloadditions in good yields, with high regio- and diastereocontrol. Cyclobutane-containing bi- tri- and tetracylic scaffolds were successfully prepared, with broad tolerance toward functional groups relevant to drug discovery campaigns. Fluorescence quenching experiments, time-correlated single-photon counting, and transient absorption spectroscopy were also conducted to provide insight into the reaction and evidence for an EnT mechanism.This work describes the performance of imidazoacridine-based TADF materials for visible-light mediated triplet–triplet EnT photocatalysis. 相似文献
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Tikhomirov G Oderinde M Makeiff D Mansouri A Lu W Heirtzler F Kingsley S Kwok DY Fenniri H 《The Journal of organic chemistry》2008,73(11):4248-4251
Eleven self-complementary G/\C derivatives bearing hydrophobic moieties were synthesized and characterized. One representative derivative from this family was shown to self-assemble into rosette nanotubes in hexane and form Langmuir-Blodgett films at the air-water interface. 相似文献
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Back Cover: Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross‐Coupling of Primary Aryl Amines with Aryl Halides (Angew. Chem. Int. Ed. 42/2016) 下载免费PDF全文
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Proximate composition of the seeds and chemical analysis of the oils of Lonchocarpus sericeus and Lonchocarpus cyanescens were determined. The oil content of the seed of L. cyanescens is 29.71?±?0.20% while that of L. sericeus is 28.00?±?0.50%. The seeds as well as the oils of L. cyanescens and L. sericeus were found to be rich in K, Na and Fe. Linolenic (C18:3) and oleic (C18:1) acid are the dominant fatty acids while the neutral lipids the dominant lipid class in the oils. Phytol, sterols, beta-tocopherol and hydrocarbons were identified in the unsaponifiable matters of the oils using GC-MS. The HPLC results revealed the presence of glycolipids, which are monogalactosyldiacylglycerol, digalactosyldiacylglycerol, digalactosylmonoacylglycerol and monogalactosylmonoacylglycerol. Molecular speciation of the triacylglycerol revealed the presence of molecular species with equivalent carbon chain numbers C(36) (L. sericeus) and C(50) (L. cyanescens) to be dominantly present in the oils. 相似文献