- Photoassisted Cross-Coupling Reaction of α-Chlorocarbonyl Compounds with Arylboronic Acids
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A Suzuki-Miyaura cross-coupling reaction of α-chloroacetates or α-chloroacetamides with arylboronic acids is made possible by visible-light irradiation. This reaction provides a useful method for the synthesis of α-arylacetates and α-arylacetamides from chlorides under mild reaction conditions. An indole-3-acetic acid derivative that is the key intermediate of the plant hormone auxin can be synthesized from 1-Boc-indole in two steps by combining an iridium-catalyzed C-H borylation and a palladium-catalyzed cross-coupling reaction.
- Miura, Tomoya,Murakami, Masahiro,Oku, Naoki
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supporting information
p. 1616 - 1619
(2022/03/14)
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- Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics
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A newly developed robust catalyst [Ir(COD)(Phen)Cl] (A) was used for the C-H borylation of three dozen aromatics and heteroaromatics with excellent yield and selectivity. Activation of the catalyst was identified by the use of catalytic amounts of water, alcohols, etc., when B2pin2 was used in noncoordinating solvents, while for THF catalytic use of HBpin was required. The results were on par with the in situ based expensive system [Ir(OMe)(COD)]2/dtbbpy or Me4Phen.
- Slack, Eric D.,Colacot, Thomas J.
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p. 1561 - 1565
(2021/02/20)
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- Tricepyridinium-inspired QACs yield potent antimicrobials and provide insight into QAC resistance
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Quaternary ammonium compounds (QACs) comprise a large class of surfactants, consumer products, and disinfectants. The recently-isolated QAC natural product tricepyridinium bromide displays potent inhibitory activity against S. aureus but due to its unique structure, its mechanism of action remains unclear. A concise synthetic route to access tricepyridinium analogs was thus designed and four N-alkyl compounds were generated in addition to the natural product. Biological analysis of these compounds revealed that they display remarkable selectivity towards clinically-relevant Gram-positive bacteria exceeding that of commercially-available QACs such as cetylpyridinium chloride (CPC) and benzalkonium chloride (BAC) while having little to no hemolytic activity. Molecular modeling studies revealed that tricepyridinium and shorter-chain N-alkyl analogs may preferentially bind to the QacR transcription factor leading to potential activation of the QAC resistance pathway found in MRSA; however, our newly synthesized analogs are able to overcome this liability.
- Garrison, Michelle A.,Mahoney, Andrew R.,Wuest, William M.
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supporting information
p. 463 - 466
(2020/10/19)
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- Small-molecule anti-HIV-1 agents based on HIV-1 capsid proteins
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The capsid of human immunodeficiency virus type 1 (HIV-1) is a shell that encloses viral RNA and is highly conserved among many strains of the virus. It forms a conical structure by assembling oligomers of capsid (CA) proteins. CA dysfunction is expected to be an important target of suppression of HIV-1 replication, and it is important to understand a new mechanism that could lead to the CA dysfunction. A drug targeting CA however, has not been developed to date. Hydrophobic interactions between two CA molecules via Trp184/Met185 in CA were recently reported to be important for stabilization of the multimeric structure of CA. In the present study, a small molecule designed by in silico screening as a dipeptide mimic of Trp184 and Met185 in the interaction site, was synthesized and its significant anti-HIV-1 activity was confirmed. Structure activity relationship (SAR) studies of its derivatives were performed and provided results that are expected to be useful in the future design and development of novel anti-HIV agents targeting CA.
- Kobayakawa, Takuya,Yokoyama, Masaru,Tsuji, Kohei,Fujino, Masayuki,Kurakami, Masaki,Boku, Sayaka,Nakayama, Miyuki,Kaneko, Moemi,Ohashi, Nami,Kotani, Osamu,Murakami, Tsutomu,Sato, Hironori,Tamamura, Hirokazu
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- Two Ligands Transfer from Ag to Pd: En Route to (SIPr)Pd(CF2H)(X) and Its Application in One-Pot C-H Borylation/Difluoromethylation
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A process for the concurrent transfer of both the NHC ligand and the difluoromethyl group from [(SIPr)Ag(CF2H)] to PdX2 (X = Cl, OAc, and OPiv) for the preparation of [(SIPr)Pd(CF2H)X] complexes is described. These complexes were air-stable and easily underwent transmetalation with aryl pinacol boronate/reductive elimination to generate ArCF2H in high yields. Based on this discovery, the first one-pot C-H borylation and difluoromethylation process for the preparation of difluoromethylated (hetero)arenes was developed.
- Herbert, Simon,Kinzel, Tom,Shen, Qilong,Zhang, Wei,Zhao, Haiwei
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p. 3596 - 3604
(2020/03/23)
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- Hyrtinadine alkaloid derivative as well as preparation and application of Hyrtinadine alkaloid derivative in resisting plant viruses and germs
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The invention relates to a Hyrtinadine alkaloid derivative as well as preparation and application of the Hyrtinadine alkaloid derivative in resisting plant viruses and germs. The Hyrtinadine alkaloidderivative shows especially excellent plant virus resist
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Paragraph 0034; 0041
(2020/02/17)
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- BENZYLAMINE COMPOUND, AND PHARMACEUTICAL COMPOSITION AND ANTI-HIV AGENT THEREOF
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PROBLEM TO BE SOLVED: To provide: a novel benzylamine compound; and a pharmaceutical composition and an anti-HIV agent that are suitable for suppression of HIV activity. SOLUTION: The benzylamine compound is represented by the general formula (1) in the figure. In the general formula (1), R1 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; A represents an oxygen atom or sulfur atom; R2 represents a substituted or unsubstituted alkyl group; and n represents an integer from 1 to 10. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0070; 0072-0073
(2020/05/13)
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- Double N,B-Type Bidentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C-H Borylation
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Boryl ligands hold promise in catalysis due to their very high electron-donating property. In this communication double N,B-type boryl anions were designed as bidentate ligands to promote an sp2 C-H borylation reaction. A symmetric pyridine-con
- Wang, Guanghui,Xu, Liang,Li, Pengfei
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supporting information
p. 8058 - 8061
(2015/07/15)
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- Iridium-catalyzed C-H borylation of heterocycles using an overlooked 1,10-phenanthroline ligand: Reinventing the catalytic activity by understanding the solvent-assisted neutral to cationic switch
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The preformed catalyst [Ir(Cl)(COD)(1,10-phenanthroline)] (2; COD = cyclooctadiene) was found to be highly effective in a model reaction for the borylation of N-Boc-indole at the 3-position with B2pin2 (pin = pinacolato) as the borylating agent to give consistently 99% yield with 0.5 mol % catalyst loading. The corresponding in situ formed catalyst from [Ir(Cl)(COD)]2 and 1,10-phenanthroline provided very inconsistent results for the same reaction (0-94% conversion). We propose this to be due to the competing formation of a catalytically inactive cationic complex, [Ir(COD)(1,10-phenanthroline)]+Cl- (1), in a noncoordinating solvent such as octane. Complexes 1 and 2 were characterized using solid-state NMR (13C and 35Cl) in conjunction with XPS to be cationic and neutral, respectively. The X-ray crystal structure of a pentavalent neutral Ir complex, [Ir(Cl)(COD)(2,2′-bipyridine)] (3), was also obtained for comparison purposes. Using catalyst 2, the total synthesis of Meridianin G was accomplished in 87% overall isolated yield in a one-pot, three-step process.
- Seechurn, Carin C. C. Johansson,Sivakumar, Vilvanathan,Satoskar, Deepak,Colacot, Thomas J.
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p. 3514 - 3522
(2014/08/05)
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- Asymmetric synthesis of 1-heteroaryl-1-arylalkyl tertiary alcohols and 1-pyridyl-1-arylethanes by lithiation-borylation methodology
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The synthesis of highly enantioenriched α-heterocyclic tertiary alcohols has been achieved via lithiation-borylation of a configurationally stable lithiated carbamate and heterocyclic pinacol boronic esters followed by oxidation. Protodeboronation of the α-heterocyclic tertiary boronic esters using TBAF·3H2O or CsF gave highly enantioenriched 1-pyridyl-1-arylethanes in high er.
- Watson, Charlotte G.,Aggarwal, Varinder K.
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supporting information
p. 1346 - 1349
(2013/05/09)
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- One-pot synthesis of camalexins and 3,3′-biindoles by the Masuda borylation-Suzuki arylation (MBSA) sequence
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The Masuda borylation/Suzuki arylation (MBSA) sequence starting from N-protected 3-iodoindoles has successfully been extended to the coupling of five-membered heterocycles and indoles in the arylation step, which could not be achieved with previously developed MBSA methods. By this approach the one-pot nature of the method as well as the use of a simple catalyst system has been retained. The applicability of the method has been demonstrated by the facile synthesis of camalexins and 3,3′-biindoles, compounds of special interest due to their pronounced antifungal, antimicrobial and cytotoxic activities. The Masuda borylation/Suzuki arylation sequence furnishes in a concise one-pot manner camalexins and 3,3′-biindoles, compounds that show pronounced antifungal, antimicrobial, and cytotoxic activities. Copyright
- Tasch, Boris O. A.,Antovic, Dragutin,Merkul, Eugen,Mueller, Thomas J. J.
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p. 4564 - 4569
(2013/07/26)
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- Highly selective trifluoromethylation of 1,3-disubstituted arenes through iridium-catalyzed arene borylation
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The old one two: A sequential iridium-catalyzed borylation and copper-catalyzed trifluoromethylation of arenes is described (see scheme; Pin=pinacol). The reaction is conducted under mild reaction conditions and tolerates a variety of functional groups. T
- Liu, Tianfei,Shao, Xinxin,Wu, Yaming,Shen, Qilong
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supporting information; experimental part
p. 540 - 543
(2012/03/11)
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- One-pot synthesis of diazine-bridged bisindoles and concise synthesis of the marine alkaloid hyrtinadine A
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Diazine-bridged bisindoles are readily obtained from N-Bocprotected 3-iodoindoles and 3-iodo-7-azaindole in a pseudo three-component reaction involving a one-pot Masuda borylation-Suzuki arylation sequence. Some of the title com-pounds display promising c
- Tasch, Boris O. A.,Merkul, Eugen,Mueller, Thomas J. J.
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p. 4532 - 4535
(2011/10/03)
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- Rapid synthesis of bis(hetero)aryls by one-pot Masuda borylation-Suzuki coupling sequence and its application to concise total syntheses of meridianins A and G
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3-(Hetero)aryl substituted indoles, 7-azaindoles, and pyrroles can be obtained in a very concise fashion via a one-pot Masuda borylation-Suzuki coupling sequence. The concise total syntheses of the marine natural products meridianins A (5) and G (4i) nice
- Merkul, Eugen,Schaefer, Elisabeth,Mueller, Thomas J. J.
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supporting information; experimental part
p. 3139 - 3141
(2011/06/28)
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- Pyrrolydine Derivatives as IAP Inhibitors
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The present invention relates to novel IAP inhibitor compounds of: Formula (I).
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Page/Page column 42-44
(2011/02/18)
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- Boc groups as protectors and directors for ir-catalyzed C-H borylation of heterocycles
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(Chemical Equation Presented) Ir-catalyzed C-H borylation is found to be compatible with Boc protecting groups. Thus, pyrroles, indoles, and azaindoles can be selectively functionalized at C-H positions β to N. The Boc group can be removed on thermolysis
- Kallepalli, Venkata A.,Shi, Feng,Paul, Sulagna,Onyeozili, Edith N.,Maleczka Jr., Robert E.,Smith III, Milton R.
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supporting information; experimental part
p. 9199 - 9201
(2010/03/02)
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