- Metal-Free Regioselective Chloroazidation of Internal Alkynes
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A metal-free, room temperature protocol for the regioselective chloroazidation of internal alkynes is disclosed. The reactions of internal alkynes with trimethylsilyl azide (TMSN3) in the presence of 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) afforded the corresponding chloroazidoalkenes in good yields. This reaction has good functional group tolerance and is operationally simple.
- Huang, Bin,Liffert, Raphael,Linden, Anthony,Gademann, Karl
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supporting information
p. 981 - 984
(2019/01/04)
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- Palladium-catalyzed multicomponent reaction (MCR) of propargylic carbonates with isocyanides
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A palladium-catalyzed multicomponent reaction (MCR) of propargylic carbonates with isocyanides is reported. Remarkably, the orderly insertion of isocyanides affords two types of valuable N-heterocyclic products (Z)-6-imino-4,6-dihydro-1H-furo[3,4-b]pyrrol-2-amines and (E)-5-iminopyrrolones in high yields. Systematic analysis of the reaction conditions indicates that the selectivity of these N-heterocyclic products can be controlled by ligands and temperature.
- Peng, Jianwen,Gao, Yang,Hu, Weigao,Gao, Yinglan,Hu, Miao,Wu, Wanqing,Ren, Yanwei,Jiang, Huanfeng
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supporting information
p. 5924 - 5927
(2016/11/29)
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- Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes
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(Chemical Equation Presented) "Cu-CF3" species have been used historically for a broad spectrum of nucleophilic trifluoromethylation reactions. Although recent advancements have employed ligands to stabilize and harness the reactivity of this key organometallic intermediate, the ability of a ligand to differentiate a regiochemical outcome of a Cu-CF3-mediated or -catalyzed reaction has not been previously reported. Herein, we report the first example of a Cu-catalyzed trifluoromethylation reaction in which a ligand controls the regiochemical outcome. More specifically, we demonstrate the ability of bipyridyl-derived ligands to control the regioselectivity of the Cu-catalyzed nucleophilic trifluoromethylation reactions of propargyl electrophiles to generate (trifluoromethyl)allenes. This method provides a variety of di-, tri-, and tetrasubstituted (trifluoromethyl)allenes, which can be further modified to generate complex fluorinated substructures.
- Ambler, Brett R.,Peddi, Santosh,Altman, Ryan A.
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supporting information
p. 2506 - 2509
(2015/05/27)
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- Synthesis of naphthalene amino esters and arylnaphthalene lactone lignans through tandem reactions of 2-alkynylbenzonitriles
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Tandem reaction of 2-alkynylbenzonitriles with a Reformatsky reagent turned out to be a novel and efficient approach toward 1-aminonaphthalene-2- carboxylates. Interestingly, with 2-(3-hydroxyprop-1-ynyl)benzonitriles as the substrates, a more sophisticat
- He, Yan,Zhang, Xinying,Fan, Xuesen
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supporting information
p. 5641 - 5643
(2014/05/20)
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- Palladium-tetraphosphine complex: An efficient catalyst for the alkynylation of ortho-substituted aryl bromides
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The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane in combination with [Pd(C3H5)Cl]2 affords a very efficient catalyst for the alkynylation of ortho-substituted aryl bromides. A wide variety of substituents such as phenyl, trifluoromethyl, acetyl, formyl or nitrile, are tolerated. High turnover numbers can be obtained with most of these aryl bromides. The coupling of sterically very congested aryl bromides such as 9-bromoanthracene or 2,4,6-triisopropylbromobenzene also proceeds in good yields.
- Feuerstein, Marie,Berthiol, Florian,Doucet, Henri,Santelli, Maurice
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p. 1281 - 1289
(2007/10/03)
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