- Ruthenium-Catalyzed Propargylic Reduction of Propargylic Alcohols with Hantzsch Ester
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Ruthenium-catalyzed propargylic reduction of propargylic alcohols bearing a terminal alkyne moiety is accomplished by using Hantzsch ester as a nucleophilic hydride source. A variety of secondary and tertiary propargylic alcohols are reduced to the corresponding propargylic reduced products such as 1-alkynes in excellent yields. Some mechanistic studies indicate that ruthenium-allenylidene complexes may work as key reactive intermediates.
- Ding, Haowei,Sakata, Ken,Kuriyama, Shogo,Nishibayashi, Yoshiaki
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supporting information
p. 2130 - 2134
(2020/06/08)
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- Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates
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Cyanophosphates (CPs) can be easily prepared from either ketones or aldehydes, and their reaction with NaN3-Et3N·HCl results in the formation of azidotetrazoles. Under microwave irradiation, successive fragmentation of the azidotetrazoles generates alkylidene carbenes that undergo [1,2]-rearrangement and are transformed into homologous alkynes. Treatment of ketone-derived CPs with TMSN3 and Bu2SnO as catalyst in toluene at reflux directly yields the corresponding internal alkynes, whereas the reaction of aldehyde-derived CPs with NaN3-Et3N·HCl in THF at reflux or TMSN3-Bu2SnO (cat.) in toluene at reflux provides homologous terminal alkynes in good yields. These reactions take place under neutral conditions and can be successfully extended to obtain alkynes that are not usually accessible from the corresponding carbonyl compounds by the Ohira-Bestmann or Shioiri procedures, which require basic conditions.
- Yoneyama, Hiroki,Numata, Masahiro,Uemura, Kenji,Usami, Yoshihide,Harusawa, Shinya
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p. 5538 - 5556
(2017/06/07)
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- Biarylphosphonite gold(I) complexes as superior catalysts for oxidative cyclization of propynyl arenes into indan-2-ones
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Striking gold: A series of variously functionalized propynyl arenes was smoothly converted into indan-2-ones by a new gold(I)-catalyzed oxidative cyclization process. [LAu]NTf2 (Tf=trifluoromethanesulfonyl) is a superior catalyst both in terms of yield and kinetics for the present transformation. Copyright
- Henrion, Guilhem,Chavas, Thomas E. J.,Le Goff, Xavier,Gagosz, Fabien
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supporting information
p. 6277 - 6282
(2013/07/11)
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- Removal of human ether-à-go-go related gene (hERG) K+ channel affinity through rigidity: A case of clofilium analogues
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Cardiotoxicity is a side effect that plagues modern drug design and is very often due to the off-target blockade of the human ether-à-go-go related gene (hERG) potassium channel. To better understand the structural determinants of this blockade, we design
- Louvel, Julien,Carvalho, Jo?o F.S.,Yu, Zhiyi,Soethoudt, Marjolein,Lenselink, Eelke B.,Klaasse, Elisabeth,Brussee, Johannes,Ijzerman, Adriaan P.
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p. 9427 - 9440
(2014/01/06)
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- Chiral Carbenoids: Their Formation and Reactions
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Carbenoids, generated by metalation or halogen-metal exchange reactions, have been prepared from chiral vinyl and cyclopropyl halides.The reactivity and stereochemistry observed in the reaction of these carbenoids has been interpreted as being due to meta
- Topolski, M.,Duraisamy, M.,Rachon, J.,Gawronski, J.,Gawronska, K.,et al.
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p. 546 - 555
(2007/10/02)
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- Allene/haloolefin electrocyclic reactions: A new route to stable triarylmethyl radicals
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Electrocyclization of allene 1,1-diphenyl-3-[2-(2-bromoethenyl)phenyl]propadiene (5), followed by one-electron reduction with elemental mercury, gives β-naphthyldiphenylmethyl radical 6 in good yield. In the absence of mercury, the only product isolated i
- Porter, Ned A.,Hogenkamp, Derk J.,Khouri, Farid F.
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p. 2402 - 2407
(2007/10/02)
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- DEOXYGENATION OF ACETYLENIC CARBINOLS. REDUCTION OF COBALT CARBONYL ADDUCTS WITH BORANE-METHYL SULFIDE AND TRIFLUOROACETIC ACID
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Diverse acetylenic carbinols were deoxygenated in 35-85percent yield by reduction of their dicobalt hexacarbonyl complexes with borane-methyl sulfide and trifluoroacetic acid.
- McComsey, David F.,Reitz, Allen B.,Maryanoff, Cynthia A.,Maryanoff, Bruce E.
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p. 1535 - 1550
(2007/10/02)
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