- The hydrodebromination of 1,1-dibromoalkenes via visible light catalysis
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Vinyl bromides are versatile synthetic intermediates and widely applied in organic synthesis and pharmaceuticals. Herein, a hydrodebromination reaction of 1,1-dibromoalkenes was established via visible light catalysis. A variety of structurally different vinyl bromides were obtained in moderate to excellent yields.
- Sun, Wencheng,Teng, Qiaoling,Cheng, Dongping,Li, Xiaonian,Xu, Xiaoliang
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supporting information
(2019/12/05)
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- Synthesis of α,ω-Bis-Enones by the Double Addition of Alkenyl Grignard Reagents to Diacid Weinreb Amides
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An efficient double addition of substituted alkenylmagnesium bromides to bis-Weinreb amides has been developed, giving α,ω-bis-enones that are building blocks for certain drugs and polymers. Furthermore, reliable protocols for the preparation of the requi
- Wiesler, Stefan,Bau, Michael A.,Niepel, Thomas,Younas, Sara L.,Luu, Hieu-Trinh,Streuff, Jan
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p. 6246 - 6260
(2019/09/10)
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- Ohmic Heating and Ionic Liquids in Combination for the Indium-Promoted Synthesis of 1-Halo Alkenyl Compounds: Applications to Pd-Catalysed Cross-Coupling Reactions
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We have explored the combination of ohmic heating (ΩH) with ionic liquids for indium-promoted reactions and report herein the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins for the synthesis of 1-halo alkenyl derivatives. Heck, Stille, Suzuki, Kumada and Sonogashira couplings of the resulting 1-halo-1-alkenes with appropriate reagents were carried out to give alkenes, dienes and enynes. We report herein the combination of ohmic heating (ΩH) with ionic liquids for the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins. The 1-halo alkenyl derivatives synthesized were then submitted to a series of cross-coupling reactions to give conjugated alkenes, dienes and enynes.
- Soengas, Raquel G.,Silva, Vera L. M.,Pinto, Joana,Rodríguez-Solla, Humberto,Silva, Artur M. S.
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- A Convenient Stereoselective Reduction of Gem-Dibromides with a Combination of Dimethyl Phosphite and Potassium Carbonate
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An efficient and highly stereoselective reduction of a gem-dibromocyclopropane to the corresponding monobromocyclopropane under mild reaction conditions was developed using a combination of dimethyl phosphite and potassium carbonate. This reaction provided a simple and practical way for the synthesis of the valuable monobromocyclopropanes and β-monobromoalkenes.
- Zhao, Yalei,Chen, Tieqiao,Wang, Xiang-Bo,Han, Li-Biao
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p. 1820 - 1827
(2015/12/12)
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- Nickel-catalyzed asymmetric reductive cross-coupling between vinyl and benzyl electrophiles
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A Ni-catalyzed asymmetric reductive cross-coupling between vinyl bromides and benzyl chlorides has been developed. This method provides direct access to enantioenriched products bearing aryl-substituted tertiary allylic stereogenic centers from simple, stable starting materials. A broad substrate scope is achieved under mild reaction conditions that preclude the pregeneration of organometallic reagents and the regioselectivity issues commonly associated with asymmetric allylic arylation.
- Cherney, Alan H.,Reisman, Sarah E.
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supporting information
p. 14365 - 14368
(2014/12/11)
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- Nickel(II)-magnesium-catalyzed cross-coupling of 1,1-dibromo-1-alkenes with diphenylphosphine oxide: One-pot synthesis of (E)-1-alkenylphosphine oxides or bisphosphine oxides
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A novel nickel(II)-magnesium-mediated cross-coupling of diphenylphosphine oxide with a variety of 1,1-dibromo-1-alkenes has been developed, which provides a powerful and general methodology for the stereoselective synthesis of various (E)-1-alkenylphosphine oxides or bisphosphine oxides, with operational simplicity of the procedure, good to high yields and broad substrate applicability. Mechanistic studies reveal that the reaction might involve a Hirao reduction, cross-coupling and Michael addition. Copyright
- Liu, Liu,Wang, Yulei,Zeng, Zhiping,Xu, Pengxiang,Gao, Yuxing,Yin, Yingwu,Zhao, Yufen
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supporting information
p. 659 - 666
(2013/04/10)
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- Ruthenium-catalyzed transformation of aryl and alkenyl triflates to halides
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Aryl triflates were transformed to aryl bromides/iodides simply by treating them with LiBr/NaI and [Cp*Ru(MeCN)3]OTf. The ruthenium complex also catalyzed the transformation of alkenyl sulfonates and phosphates to alkenyl halides under mild conditions. Aryl and alkenyl triflates undergo oxidative addition to a ruthenium(II) complex to form η'1- arylruthenium and 1-ruthenacyclopropene intermediates, respectively, which are transformed to the corresponding halides.
- Imazaki, Yusuke,Shirakawa, Eiji,Ueno, Ryota,Hayashi, Tamio
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supporting information
p. 14760 - 14763
(2012/11/07)
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- A new entry of highly nucleophilic CHBr3-TiCl4-Mg system for the stereoselective synthesis of 1-alkenyl bromides
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This TiCl4-Mg promoted coupling of CHBr3 with various aldehydes and ketones, especially in sterically hindered or enolizable ketones, provides a simple, practical, and stereoselective carbonyl-bromomethylenation leading primarily to (E)-vinyl bromides.
- Bhorge, Yeshwant Ramchandra,Chang, Su-Haur,Chang, Cheng-Ta,Yan, Tu-Hsin
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experimental part
p. 4846 - 4851
(2012/08/07)
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- A novel method for bromodecarboxylation of α,β-unsaturated carboxylic acids using catalytic sodium nitrite
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A first novel synthetic utility of catalytic sodium nitrite in combination with aqueous HBr, for bromo decarboxylation of α,β-unsaturated carboxylic acid is described. α,β-Unsaturated carboxylic acid compounds successfully converted into corresponding bromo compounds. The advantages of this protocol are shorter reaction time and moderate to good yields.
- Telvekar, Vikas N.,Takale, Balaram S.
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experimental part
p. 2394 - 2396
(2011/05/09)
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- Transfer of alk-1-enyl group from boron to tin: A highly stereoselective synthesis of (E)-alk-1-enyltributylstannanes
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Treatment of (E)-alk-1-enyldicyclohexylboranes with tributyltin methoxide in the presence of galvinoxyl (1 mol%) at room temperature results in transfer of the alk-1-enyl group from boron to tin to give (E)-alk-1- enyltributylstannanes in a highly stereoselective fashion. Subsequent halodestannylation of (E)-alk-1-enyltributylstannanes is allowed to proceed in a one-pot manner to produce the corresponding (E)-1-iodoalk-1-enes and (E)-1-bromoalk-1-enes in good to high yields, respectively. Georg Thieme Verlag Stuttgart.
- Hoshi, Masayuki,Hayatsu, Takaki,Okimoto, Mitsuhiro,Kodama, Satoshi
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scheme or table
p. 2945 - 2948
(2010/02/28)
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- Facile and stereoselective synthesis of (E)-vinyl bromides by microwave-induced reaction of 1,1-dibromoalkenes using a diethyl phosphonate/EtONa/EtOH system
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(E)-Vinyl bromides were readily prepared from 1,1-dibromoalkenes by microwave irradiation within 1 min using a diethyl phosphonate/EtONa/EtOH system. This method utilizes cheap and environmentally friendly reagents, requires only a short reaction time, and gives (E)-vinyl bromides in high stereoselectivities and high yields.
- Kuang, Chunxiang,Senboku, Hisanori,Tokuda, Masao
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p. 1491 - 1496
(2007/10/03)
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- The 'Hirao reduction' revisited: A procedure for the synthesis of terminal vinyl bromides by the reduction of 1,1-dibromoalkenes
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A convenient procedure for the synthesis of vinyl bromides is described, which involves the selective reduction of the corresponding 1,1- dibromoalkenes with dimethylphosphite and triethylamine. The 1,1- dibromoalkenes are obtained in excellent yields fro
- Abbas, Sahar,Hayes, Christopher J.,Worden, Stephen
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p. 3215 - 3219
(2007/10/03)
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- Selective debromination of 1,1-dibromoalkenes; a new access to di- or trisubstituted alkenes
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1,1-Dibromoalkenes were selectivity debrominated by halogen-metal exchange. Depending on reagents and conditions, E-bromoalkenes can be obtained with very high stereoselectivity.
- Grandjean,Pale
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p. 1155 - 1158
(2007/10/02)
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- Vinylic Organoboranes. 14. Stereospecific Synthesis of (E)-1-Halo-1-alkanes from 1-Alkynes
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The reactions of (E)-1-alkenylboronic acids and their esters and (E)-1-alkenyldibromoborane-dimethyl sulfide complexes with iodine under various conditions were investigated.All of these compounds react with iodine in the presence of base, producing (E)-1
- Brown, Herbert C.,Hamaoka, Tsutomu,Ravindran, Nair,Subrahmanyam, Chitti,Somayaji, Vishwanatha,Bhat, Narayan G.
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p. 6075 - 6079
(2007/10/02)
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- Vinylic Organoboranes. 15. Mercuration of 2-Alkenyl-1,3,2-benzodioxaboroles and Boronic Acids. A Convenient Stereospecific Procedure for the Conversion of Alkynes into (E)-1-Halo-1-alkenes via Mercuric Salts
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Vinylboranes derived from terminal and internal alkynes via hydroboration with 1,3,2-benzodioxaborole undergo an instantaneous reaction with mercuric acetate at 0 deg C to give the corresponding vinylmercuric acetates in exceptionally good yields.The reac
- Brown, Herbert C.,Larock, Richard C.,Gupta, S. K.,Rajagopalan, Shyamala,Bhat, Narayan G.
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p. 6079 - 6084
(2007/10/02)
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