- Synthesis of a photocontrollable hydrogen sulfide donor using ketoprofenate photocages
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We report the design, synthesis and application of a directly photocontrollable hydrogen sulfide (H2S) donor, which releases H 2S proportionally to the intensity and duration of photoirradiation. Photocontrolled H2S releas
- Fukushima, Naoki,Ieda, Naoya,Sasakura, Kiyoshi,Nagano, Tetsuo,Hanaoka, Kenjiro,Suzuki, Takayoshi,Miyata, Naoki,Nakagawa, Hidehiko
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- Electrochemical fluorosulfonylation of alkenes to access vicinal fluorinated sulfones derivatives
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Herein, we report a practical and efficient fluorosulfonylation of the various alkenes with sulfonyl radical sources (RSO2NHNH2) and Et3N·3HF as cost-effective fluorination reagents under mild conditions. Remarkably, this
- Zhao, Bin,Pan, Zichen,Zhu, Anqiao,Yue, Yanni,Ma, Mengtao,Xue, Fei
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supporting information
(2022/01/24)
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- 1,3-Difunctionalization of β-alkyl nitroalkenes via combination of Lewis base catalysis and radical oxidation
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Upon treatment with a Lewis base catalyst, β-alkyl-substituted nitroalkenes could be readily converted into allylic nitro compounds. Examples of either C-1 or C-3 functionalization methods have been reported through nitro-elimination, giving alkene products. In this work, successful 1,3-difunctionalization was achieved through a synergetic Lewis base catalysis and TBHP radical oxidation, giving vinylic alkoxyamines in good to excellent yields. This work further extended the general synthetic application of β-alkyl nitroalkenes.
- Wang, Ye,Zheng, Lei,Shi, Xiaodong,Chen, Yunfeng
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supporting information
p. 886 - 889
(2021/02/01)
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- Formal Allylation and Enantioselective Cyclopropanation of Donor/Acceptor Rhodium(II) Azavinyl Carbenes
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A highly efficient formal allylation of dihydronaphthotriazoles with alkenes under rhodium(II) catalysis is reported. Various allyl dihydronaphthalene derivatives were furnished via rhodium(II) azavinyl carbenes with moderate to good yields and excellent chemoselectivity. When monosubstituted alkenes are used, cyclopropanation occurs and good to excellent enantioselectivities have been achieved. Particularly noteworthy is the allylic C(sp2)-H activation instead of traditional C(sp3)-H activation in the formal allylation process.
- Liu, Zhili,Chen, Lianfen,Zhu, Dong,Zhu, Shifa
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supporting information
p. 1275 - 1279
(2021/02/20)
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- Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon
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Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes with aniline hydrochloride salts to afford amides bearing an α quaternary carbon. The reaction makes use of readily available starting materials, tolerates a wide range of functional groups, and provides a facile and straightforward approach to a diverse array of amides bearing an α quaternary carbon. Mechanistic investigations suggested that the reaction proceeded through a palladium hydride pathway. The hydropalladation and CO insertion are reversible, and the aminolysis is probably the rate-limiting step.
- Yang, Hui-Yi,Yao, Ya-Hong,Chen, Ming,Ren, Zhi-Hui,Guan, Zheng-Hui
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supporting information
p. 7298 - 7305
(2021/05/26)
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- Aqueous ZnCl2 Complex Catalyzed Prins Reaction of Silyl Glyoxylates: Access to Functionalized Tertiary α-Silyl Alcohols
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An efficient Prins reaction of silyl glyoxylates in the presence of an aqueous ZnCl2 complex as a catalyst was developed, providing functionalized tertiary α-silyl alcohols in high yields under mild conditions. A preliminary investigation indicated that the aqueous ZnCl2 complex acted as a dual functional catalyst of Br?nsted and Lewis acid to activate the carbonyl groups of silyl glyoxylates via a dual-activation model.
- Han, Man-Yi,Pan, Hong,Li, Pinhua,Wang, Lei
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p. 5825 - 5837
(2020/05/22)
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- Cobalt-Catalyzed Coupling of Benzoic Acid C?H Bonds with Alkynes, Styrenes, and 1,3-Dienes
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A method for cobalt-catalyzed, carboxylate-directed functionalization of arene C?H bonds is reported. Alkynes, styrenes, and 1,3-dienes can be coupled with benzoic acids to provide cyclic products in good yields. The reactions proceed in the presence of a
- Nguyen, Tung Thanh,Grigorjeva, Liene,Daugulis, Olafs
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supporting information
p. 1688 - 1691
(2018/01/15)
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- Water-Enabled Catalytic Asymmetric Michael Reactions of Unreactive Nitroalkenes: One-Pot Synthesis of Chiral GABA-Analogs with All-Carbon Quaternary Stereogenic Centers
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Water enables new catalytic reactions for otherwise unreactive substrate systems. Under the “on water” reaction conditions, extremely unreactive β,β-disubstituted nitroalkenes smoothly underwent enantioselective Michael addition reactions with dithiomalonates using a chiral squaramide catalyst, affording both enantiomers of highly enantioenriched Michael adducts with all-carbon-substituted quaternary centers. The developed “on water” protocol was successfully applied for the scalable one-pot syntheses of chiral GABA analogs with all-carbon quaternary stereogenic centers at the β-position, which might show highly interesting pharmaceutical properties.
- Sim, Jae Hun,Song, Choong Eui
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supporting information
p. 1835 - 1839
(2017/02/05)
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- Palladium-catalyzed oxidative allylation of bis[(pinacolato)boryl]methane: Synthesis of homoallylic boronic esters
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A palladium-catalyzed oxidative allylation of bis[(pinacolato)boryl]methane to afford the corresponding homoallylic organoboronic esters with moderate to excellent yields is reported. This novel transformation provides an efficient strategy for the construction of homoallylic organoboronic esters in one step with a broad substrate scope. It is proposed that the palladium-catalyzed oxidative allylic C-H bond activation process may be involved in the catalytic cycle.
- Li, Chunsheng,Li, Meng,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 66 - 69
(2017/12/27)
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- Synthesis of 2,5-Diaryl-1,5-dienes from Allylic Bromides Using Visible-Light Photoredox Catalysis
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Visible-light photoreductive coupling of 2-arylallyl bromides in the presence of the photocatalyst Ru(bpy)3(PF6)2, a Hantzsch ester, and i-Pr2NEt gives 2,5-diaryl-1,5-dienes in high yield. This method avoids the use of stoichiometric metal reductants and is compatible with the presence of halogen, alkyl, electron-donating, and electron-withdrawing substituents on the aromatic ring.
- Pratsch, Gerald,Overman, Larry E.
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p. 11388 - 11397
(2015/12/01)
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- Trifluoromethylation of aromatic alkenes by visible-light-driven photoredox catalysis: Direct conversion of alkenes to 3-trifluoromethyl-1-propenyl and 1,3-bis(trifluoromethyl)-1-propenyl derivatives
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Photoredox-catalyzed trifluoromethylation of alkenes using Umemoto's reagent as a CF3 source under visible light irradiation has been developed. A Ru photocatalyst, [Ru(bpy)3](PF6)2 (bpy = 2,2′-bipyridine), is useful for the present trifluoromethylation and preferable formation of 3-trifluoromethyl-1-propenyl derivatives is observed. Use of an excess amount of Umemoto's reagent readily induces double trifluoromethylation of electron-rich alkenes, resulting in 1,3-bis(trifluoromethyl)-1-propenyl skeleton.
- Asano, Masashi,Tomita, Ren,Koike, Takashi,Akita, Munetaka
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supporting information
p. 83 - 88
(2015/11/10)
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- A rhodium(I)-catalysed formal intramolecular C-C/C-H bond metathesis
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Phenylcyclobutanes underwent skeletal reorganisation in the presence of Wilkinson's catalyst to afford indanes through a cascade process involving chelation-assisted C-C bond cleavage and intramolecular C-H bond cleavage.
- Matsuda, Takanori,Yuihara, Itaru
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supporting information
p. 7393 - 7396
(2015/04/27)
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- CYCLOALKYL NITRILE PYRAZOLO PYRIDONES AS JANUS KINASE INHIBITORS
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Compounds of formula I are provided, which are JAK inhibitors and are useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer.
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Page/Page column 108
(2014/10/03)
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- CYCLOALKYL NITRILE PYRAZOLO PYRIDONES AS JANUS KINASE INHIBITORS
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The instant invention provides compounds of formula I which are JAK inhibitors, and as such are useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer.
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Page/Page column 87
(2014/10/03)
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- Highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes
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Building the building blocks: A highly enantioselective hydrogenation of ?-aryl-?-alkyl disubstituted nitroalkenes 1 has been developed. This method results in enantiomerically pure nitroalkanes 2, which are versatile precursors for chemical synthesis.
- Li, Shengkun,Huang, Kexuan,Cao, Bonan,Zhang, Jiwen,Wu, Wenjun,Zhang, Xumu
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supporting information; experimental part
p. 8573 - 8576
(2012/09/10)
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- Method for synthesizing (E)-Anethol and Related Compounds By Cross Coupling Reaction of Potassium alllyltrifluroborate and 4-bromoanisole and aryl halides
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Methods of producing substituted and non-substituted beta-methyl styrene by a cross-coupling reaction are provided. The disclosure also provides for methods of preparing (E)-Anethol and related compounds by a cross coupling reaction of potassium allyltrifluoroborate and 4-bromoanisole and aryl halides. Compounds, compositions, and methods of treating disorders utilizing beta-methyl styrene are also provided.
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Page/Page column 4
(2012/01/15)
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- Enantioselective desymmetrization of cyclopropenes by hydroacylation
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We report an enantioselective desymmetrization of cyclopropenes by intermolecular Rh-catalyzed hydroacylation. Cyclopropylketones, bearing quaternary stereocenters, are produced with diastereocontrol (up to >20:1) and excellent enantiomeric excess (up to >99 ee).
- Phan, Diem H. T.,Kou, Kevin G. M.,Dong, Vy M.
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supporting information; experimental part
p. 16354 - 16355
(2011/02/24)
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- BACE INHIBITORS
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The present invention provides BACE inhibitors of Formula I: methods for their use, and intermediates and methods for their preparation.
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Page/Page column 18
(2009/12/02)
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- ANTIDIABETIC OXAZOLIDINEDIONES AND THIAZOLIDINEDIONES
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Phenoxyphenyl and phenoxybenzyl oxazolidine-2,4-diones and thiazolidine-2,4-diones are agonists or partial agonists of PPAR gamma and are useful in the treatment and control of hyperglycemia that is symptomatic of type II diabetes, as well as dyslipidemia
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Page/Page column 27
(2010/11/25)
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- Comparative approaches toward diamines containing spatially separated homobenzylic and benzylic nitrogen stereocenters
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Several synthetic strategies to diamines 1-3 are described. The optimum approach via opening of aziridine afforded 1-3 in 29-60% yield over 3-5 steps. A study on formation of the benzylic stereocenter using Toste's rhenium-catalyzed asymmetric reduction of phosphinyl ketimines was also evaluated and afforded 15 in 92% de.
- Achmatowicz, Michal,Chan, Johann,Wheeler, Philip,Liu, Longbin,Faul, Margaret M.
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p. 4825 - 4829
(2008/02/05)
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- ANTIDIABETIC OXAZOLIDINEDIONES AND THIAZOLIDINEDIONES
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Pyridinyloxyphenyl and pyridinyloxybenzyl oxazolidine-2,4-diones and thiazolidine-2,4-diones are agonists or partial agonists of PPAR gamma and are useful in the treatment and control of hyperglycemia that is symptomatic of type II diabetes, as well as dy
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Page/Page column 21-22
(2008/06/13)
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- ANTIDIABETIC OXAZOLIDINEDIONES AND THIAZOLIDINEDIONES
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Phenoxyphenyl and phenoxybenzyl oxazolidine-2,4-diones and thiazolidine-2,4-diones of formula (I) are agonists or partial agonists of PPAR gamma and are useful in the treatment and control of hyperglycemia that is symptomatic of type II diabetes, as well
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Page/Page column 24
(2010/02/13)
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- Alkyliron and Alkylcobalt Reagents, IV.- High Superiority of Me4CoLi2 and Me4FeLi2 in Comparison to Me2CuLi and Me4MnLi2 in Cross Coupling Reactions with Vinyl Bromides
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The complexes Me4MLi2 (M = Co, Fe, Mn) and Me2CuLi (prepared in situ, but well-known in isolated form) were treated with a series of vinyl bromides.In nearly all cases Me4CoLi2 and Me4FeLi2 proved to by far the best methylating reagents (high yields, reaction at -78 deg C, short reaction time, no excess of the reagent necessary.These reagents will tolerate a hydroxy or cyano group in the substrate, whereas the classical reagent for methylation of vinyl bromides, Me2CuLi, is strongly inhibited by these groups.With the methylation of hydroxyvinyl bromides a new method was found for the synthesis of allyl alcohols. Key Words: Organocobalt complexes / Organoiron complexes
- Kauffmann, Thomas,Stach, Dirk
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p. 913 - 922
(2007/10/02)
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- Electronic Effects on Triplet and Singlet Excited-State Carbonyl Formation in the Thermolysis 3-Aryl-3-methyl-1,2-dioxetanes
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A series of para- and meta-substituted 3-aryl-3-methyl-1,2-dioxetanes (1) was studied in order to evaluate the electronic effect of substituents on the efficiencies of excited-state carbonyl production.All substituents reduced the efficiency of triplet carbonyl production.Several correlations point to the formation of a triplet carbonyl exciplex, originating from a triplet biradical, in the thermolysis of 1.It also appears that substituent variation in the proacetophenone portion of 1 results in triplet efficiency changes primarily in formaldehyde, which can be rationalized in terms of a triplet exciplex.Substituent effects on singlet (S1) efficiency are markedly different from those observed with triplet efficiencies.The possibility of heavy-atom effects in 1 was pursued with p-Br and m-Br substituents.No detectable heavy-atom effect was observed with singlet (S1) efficiencies, but the p-Br substituent appeared to decrease the triplet efficiency.This suggests that a p-Br heavy-atom effect may operate from the triplet exciplex, providing the approximations used in the evaluations of the heavy-atom effect are valid.The effect of substituents on rate of thermolysis of 1 provides further evidence for a biradical mechanism.
- Richardson, William H.,Stiggal-Estberg, Diana L.
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p. 4173 - 4179
(2007/10/02)
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