- Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes
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A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti
- Hu, Dandan,Liu, Jiayue,Ren, Hongjun,Song, Jinyu,Zhang, Jun-Qi,Zhu, Guorong
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supporting information
p. 786 - 790
(2022/01/28)
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- Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst
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A highly efficient, direct C(sp3)-H cyanation was developed under mild photocatalytic conditions. The method enabled the direct cyanation of various C(sp3)-H substrates with excellent functional group tolerance. Notably, complex natural products and bioactive compounds were efficiently cyanated.
- Kim, Kunsoon,Lee, Seulchan,Hong, Soon Hyeok
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supporting information
p. 5501 - 5505
(2021/07/26)
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- Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles
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A metal-free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β-cyano esters, α-aryl alkylnitriles, and TBS-protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).
- Pirola, Margherita,Faverio, Chiara,Orlandi, Manuel,Benaglia, Maurizio
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supporting information
p. 10247 - 10250
(2021/06/18)
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- Lithiation Substitution of Unprotected Benzyltetrazoles
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1H-Tetrazoles occupy an important role in modern medicinal chemistry, but few methods for their modification exist. Many extant protocols require the use of a difficult to remove N-alkyl-protecting group, precluding the products from use as carboxylate bioisosteres, the major role of tetrazoles in pharmaceuticals. We herein report a convenient, protecting-group-free lithiation-substitution protocol for benzylic tetrazoles. Metalation with n-BuLi at 0 °C followed by electrophilic trapping gave a range of α-functionalized benzyltetrazoles in up to 91% yield.
- Wong, Jeff Y. F.,Lewandowska, Agnieszka,Trowse, Benjamin R.,Barker, Graeme
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p. 7069 - 7072
(2019/09/30)
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- Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source
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A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity thiocyanate salts, and a broad substrate scope.
- Huang, Yubing,Yu, Yue,Zhu, Zhongzhi,Zhu, Chuanle,Cen, Jinghe,Li, Xianwei,Wu, Wanqing,Jiang, Huanfeng
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p. 7621 - 7627
(2017/07/26)
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- One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions
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A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.
- Ezawa, Masatoshi,Togo, Hideo
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p. 2379 - 2384
(2017/05/01)
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- Synthesis method of pyrimethamine drug intermediate p-chlorobenzonitrile
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The invention relates to a synthesis method of a pyrimethamine drug intermediate p-chlorobenzonitrile, which comprises the following steps: adding 1.3 mol of p-benzyl chloride and 0.56 mol of stannous chloride into a reaction vessel which is provided with a stirrer, a thermometer, a reflux condenser and a dropping funnel, controlling the stirring rate at 130-160 rpm, heating the solution to 90-95 DEG C, slowly and dropwisely adding 1.5-1.7 mol of cyanamide within 1-2 hours, continuing stirring to react for 4-5 hours, cooling the solution to 10-15 DEG C, adding 230ml of sodium chloride solution, separating out the water layer, washing the oil layer with a salt solution, washing with acetonitrile, carrying out reduced pressure distillation, and recrystallizing the fraction in ethyl acetate to obtain the crystal p-chlorobenzonitrile, wherein the mass percent of the sodium chloride solution is 15-20%, and the salt solution is any one of potassium bromide and sodium nitrate.
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-
Paragraph 0015; 0016
(2016/11/14)
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- Construction of enantioenriched polysubstituted hexahydropyridazines via a sequential multicatalytic process merging palladium catalysis and aminocatalysis
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An efficient multicatalytic strategy for the construction of nitrogen-containing heterocycles has been reported. The powerful combination of organic and metal catalysis in a single vessel allowed the formation of enantioenriched polysubstituted cyclic 6-membered hydrazines bearing a quaternary stereocenter in good yields and selectivities.
- Marques,Giardinetti,Marrot,Coeffard,Moreau,Greck
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p. 2828 - 2832
(2016/03/12)
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- Two-step cyanomethylation protocol: Convenient access to functionalized aryl- and heteroarylacetonitriles
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A two-step protocol has been developed for the introduction of cyanomethylene groups to metalated aromatics through the intermediacy of substituted isoxazoles. A palladium-mediated cross-coupling reaction was used to introduce the isoxazole unit, followed by release of the cyanomethylene function under thermal or microwave-assisted conditions. The intermediate isoxazoles were shown to be amenable to further functionalization prior to deprotection of the sensitive cyanomethylene motif, allowing access to a wide range of aryl- and heteroaryl-substituted acetonitrile building blocks.
- Lindsay-Scott, Peter J.,Clarke, Aimee,Richardson, Jeffery
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p. 476 - 479
(2015/03/05)
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- Ametoctradin is a Potent Qo Site Inhibitor of the Mitochondrial Respiration Complex III
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Ametoctradin is a new Oomycete-specific fungicide under development by BASF. It is a potent inhibitor of the bc1 complex in mitochondrial respiration. However, its detailed action mechanism remains unknown. In the present work, the binding mode of ametoctradin was first uncovered by integrating molecular docking, MD simulations, and MM/PBSA calculations, which showed that ametoctradin should be a Qo site inhibitor of bc1 complex. Subsequently, a series of new 1,2,4-triazolo[1,5-a]pyrimidine derivatives were designed and synthesized to further understand the substituent effects on the 5- and 6-position of 1,2,4-triazolo[1,5-a]pyrimidine. The calculated binding free energies (ΔGcal) of newly synthesized analogues as Qo site inhibitors correlated very well (R2 = 0.96) with their experimental binding free energies (ΔGexp). Two compounds (4a and 4c) with higher inhibitory activity against porcine SQR than ametoctradin were successfully identified. The structural and mechanistic insights obtained from the present study will provide a valuable clue for future designing of a new promising bc1 inhibitor.
- Zhu, Xiaolei,Zhang, Mengmeng,Liu, Jingjing,Ge, Jingming,Yang, Guangfu
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p. 3377 - 3386
(2015/04/14)
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- Ionic liquid-induced conversion of methoxymethyl-protected alcohols into nitriles and iodides using [Hmim][NO3]
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This Letter reports a one-pot efficient conversion of methoxymethyl-ethers into their corresponding nitriles and iodides using the ionic liquid, 1-methyl-3H-imidazolium nitrate ([Hmim][NO3]) under microwave irradiation. A variety of products were prepared in high yields using this method.
- Noei, Jalil,Mirjafari, Arsalan
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supporting information
p. 4424 - 4426
(2014/08/05)
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- Synthesis of α-aryl esters and nitriles: Deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids
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Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds into C(sp3)-C(sp2) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. Touch base: A transition-metal-free protocol for the synthesis of α-aryl esters and nitriles by deaminative coupling is presented. Strong bases and transition-metal catalysts are not needed. The new synthetic method uses readily available starting materials and demonstrates wide substrate scope.
- Wu, Guojiao,Deng, Yifan,Wu, Chaoqiang,Zhang, Yan,Wang, Jianbo
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supporting information
p. 10510 - 10514
(2016/02/18)
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- One-pot synthesis of nitriles from aldehydes catalyzed by deep eutectic solvent
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The choline chloride-urea (1:2) based deep eutectic mixture as an efficient and ecofriendly catalyst for the one-pot synthesis of nitriles from aldehydes under solvent-free conditions under both conventional and microwave irradiation; the products were obtained in good to excellent yields. Georg Thieme Verlag Stuttgart New York.
- Patil, Umakant B.,Shendage, Suresh S.,Nagarkar, Jayashree M.
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p. 3295 - 3299
(2013/12/04)
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- One-pot conversion of aldehyde sodium bisulfites into nitriles
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Direct conversion of aldehyde sodium bisulfites to the corresponding nitriles can be easily performed by the reaction of an aldehyde sodium bisulfites with a slight execss of hydroxylamine hydrochloride in refluxing toluene and in the presence of 1.0 equivalents of pyridine as catalyst.
- Zhu, Jintao,Song, Guangwei,Yao, Guoxin,Chen, Gang
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experimental part
p. 1934 - 1940
(2012/06/01)
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- Copper-catalyzed cyanation of benzyl chlorides with non-toxic K 4[Fe(CN)6]
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Copper-based catalysts were firstly introduced into the cyanation of benzyl chlorides with non-toxic K4[Fe(CN)6]. The presented method avoids the use of extremely poisonous alkali cyanides and precious palladium catalysts. No other reagent apart from CuI, K4[Fe(CN) 6] and toluene was used in the cyanation, showing that the presented protocol is simple and practical. A series of benzyl chlorides were smoothly cyanated in up to 85% yield under the optimal conditions.
- Ren, Yunlai,Dong, Chuanhua,Zhao, Shuang,Sun, Yanpei,Wang, Jianji,Ma, Junying,Hou, Chaodong
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supporting information; experimental part
p. 2825 - 2827
(2012/07/17)
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- Pd-catalyzed cyanation of benzyl chlorides with nontoxic K 4[Fe(CN)6]
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Non-toxic K4[Fe(CN)6] was demonstrated to be effective as a green cyanating agent for the cyanation of alkyl halides using PPh3/Pd(OAc)2 as a catalyst system. The presented method allowed a series of benzyl chlorides to be smoothly cyanated in up to 88% yield. In order to avoid or suppress the deactivation of the catalyst, the reaction was required to be performed in a stringent inert ambiance.
- Ren, Yunlai,Yan, Mengjie,Zhao, Shuang,Sun, Yanpei,Wang, Jianji,Yin, Weiping,Liu, Zhifei
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scheme or table
p. 5107 - 5109
(2011/10/05)
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- Microwave-promoted, one-pot conversion of alkoxymethylated protected alcohols into their corresponding nitriles, bromides, and iodides using [bmim][InCl4] as a green catalyst
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The Lewis acid room temperature ionic liquid, [bmim][InCl4], was found to be an efficient and green catalyst for the highly chemoselective and one-pot conversion of MOM- or EOM-ethers into their corresponding nitriles, bromides, and iodides under microwave irradiation. The procedures are simple, rapid, and high yielding. The catalyst exhibited a remarkable reactivity and is reusable.
- Mirjafari, Arsalan,Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Khosropour, Ahmad Reza
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supporting information; experimental part
p. 3274 - 3276
(2010/07/18)
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- Oxidation of amidoximes with IBX and IBX/TEAB
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Biologically important process of oxidation of amidoximes has been investigated using IBX (oiodoxybenzoic acid) and combination of IBX with TEAB (tetraethylammonium bromide). The reaction proceeds with high % conversion leading to selective formation of amide and nitrile depending upon the combination of reagents. ARKAT USA, Inc.
- Deshmukh, Swapnil S.,Huddar, Sameerana N.,Bhalerao, Dinesh S.,Akamanchi, Krishnacharya G.
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experimental part
p. 118 - 126
(2010/09/05)
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- Synthesis and biological evaluation of 3,4-diaryl-5-aminoisoxazole derivatives
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A series of cis-restricted 3,4-diaryl-5-aminoisoxazoles have been synthesized and evaluated for their biological activities. Among them, compound 11a and 13a displayed potent cytotoxic activities in vitro against five human cancer cell lines with IC50 values in the low micromolar range and two compounds inhibited tubulin polymerization with IC50 value of 1.8, and 2.1 μM, respectively, similar to that of CA-4. Compound 13a could arrest at the G2/M phase of the cell cycle at the concentration of 0.1 and 1.0 μM and induce apoptosis at 0.1-1.0 μM.
- Liu, Tao,Dong, Xiaowu,Xue, Na,Wu, Rui,He, Qiaojun,Yang, Bo,Hu, Yongzhou
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scheme or table
p. 6279 - 6285
(2011/02/24)
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- Versatile and fluoride-free cyanation of alkyl halides and sulfonates with trimethylsilyl cyanide
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Cyanation of biphenyl-4-ylmethyl methanesulfonate with trimethylsilyl cyanide using fluoride-free inorganic salts, such as Cs2CO 3, K2CO3, and LiOH·H2O, as additives in MeCN quantitatively gave biphenyl-4-ylacetonitrile. This methodology was applied to various alkyl halides to give the corresponding nitrile compounds in good to excellent yields. Of note, 4-(hydroxymethyl) benzyliodide O-protected by the silyl group was converted into phenylacetonitrile derivative in 99% yield without desilylation. Georg Thieme Verlag Stuttgart.
- Yabe, Osamu,Mizufune, Hideya,Ikemoto, Tomomi
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experimental part
p. 1291 - 1294
(2009/10/23)
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- o-iodoxybenzoic acid- and tetraethylammonium bromide-mediated oxidative transformation of primary carboxamides to one-carbon dehomologated nitriles
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A clean and efficient method for the oxidative transformations of primary carboxamides to one-carbon dehomologated nitriles using the combination of o-iodoxybenzoic acid and tetraethylammonium bromide has been developed. This method exhibits a broad scope and is expected to be of great utility in organic synthesis.
- Bhalerao, Dinesh S.,Mahajan, Ulhas S.,Chaudhari, Kiran H.,Akamanchi, Krishnacharya G.
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p. 662 - 665
(2007/10/03)
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- Cyanation of alcohols with diethyl cyanophosphonate and 2,6-dimethyl-1,4-benzoquinone by a new type of oxidation-reduction condensation
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Cyanation of various alcohols by a new type of oxidation-reduction condensation is described. Primary alkyl diphenylphosphinites, 2,6-dimethyl-1,4-benzoquinone (DMBQ), and diethyl cyanophosphonate gave the corresponding nitriles in high yields. During the above experiment on cyanation of 4-phenylbutan-2-ol, the unexpected formation of a mixture of nitrile and isocyanide was observed. After careful examination of the reaction conditions, selective synthesis of isocyanides from secondary alcohols was successfully accomplished by the use of zinc oxide (ZnO) as an additive. Reaction of tertiary alcohols provided the corresponding isocyanides exclusively in the absence of an additive. Cyanation of optically active alcohols was tried in order to clarify the stereochemistry of this reaction, and the reaction was thus proved to proceed with the inversion of configuration.
- Masutani, Kouta,Minowa, Tomofumi,Hagiwara, Yoshiaki,Mukaiyama, Teruaki
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p. 1106 - 1117
(2007/10/03)
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- Preparation of nitriles from primary alcohols by a new type of oxidation-reduction condensation using 2,6-dimethyl-1,4-benzoquinone and diethyl cyanophosphonate
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Cyanation of alkoxydiphenylphosphines, in situ prepared from nBuLi and various primary alcohols, with 2,6-dimethyl-1,4- benzoquinone (DMBQ) and diethyl cyanophosphonate provided the corresponding nitriles in high yields.
- Mukaiyama, Teruaki,Masutani, Kouta,Hagiwara, Yoshiaki
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p. 1192 - 1193
(2007/10/03)
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- Conversion of Alcohols, Thiols, and Trimethysilyl Ethers to Alkyl Cyanides Using Triphenylphosphine/2,3-Dichlorol-5,6-dicyanobenzoquinone/n-Bu 4NCN
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Triphenylphosphine and 2,3-dichloro-5,6-dicyanobenzoquinone afford an adduct, which in the presence of n-Bu4NCN converts alcohols, thiols, and trimethylsilyl ethers into their corresponding alkyl cyanides in good to excellent yields at room tem
- Iranpoor, Nasser,Firouzabadi, Habib,Akhlaghinia, Batool,Nowrouzi, Najmeh
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p. 2562 - 2564
(2007/10/03)
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- Synthesis, selective aldose reductase inhibitory profile and antihyperglycaemic potential of certain parabanic acid derivatives
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Synthesis and aldose reductase inhibitory profile of certain parabanic acid derivatives 1a-p is described. Also, the antihyperglycaemic potential of these compounds was studied. The most active inhibitors in this series were compounds 1 g, 1p, and 1o which showed inhibitory activity, 36.6, 90 and 91% respectively, at concentration 1 × 10-4. Their IC50 were 2 × 10-6, 7.5 × 10-8 and 5 × 10-8, respectively. Compound 1o exhibited pronounced antihyperglycaemic effect.
- Nabil Aboul-Enein,El-Azzounya,Maklad,Attia,Wiese
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p. 329 - 350
(2007/10/03)
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- Synthesis and electronic spectra of substituted oligo(phenylenevinylene)s
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A series of substituted oligo(p-phenylenevinylene)s (OPVs) with five benzene rings was prepared via PO-activated olefinations and Knoevenagel condensations. The central ring is substituted with two octyloxy groups to ensure good solubility of the OPVs and the lateral styrene units carry further substituents, with either electron-accepting or donating character and also combinations thereof. The spectral features of these OPVs are dominated by the basic chromophore; further auxochrome groups on the lateral rings (meta and para positions) shift the absorption and emission spectra only slightly to longer wavelengths. Significant bathochromic shifts (absorption ca 20 nm, emission ca 40 nm) are observed for OPVs with cyano groups on the terminal vinylene segments. The absorption spectra are independent from the concentration and solvatochromism is very small. The OPVs are photochemically stable to near-UV irradiation (366 nm) in neutral solution, whereas mid-UV irradiation (254 nm) causes decomposition of the chromophore. The presence of traces of acids or amines leads to different photochemical pathways. Copyright
- Detert, Heiner,Sugiono, Erli
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p. 587 - 590
(2007/10/03)
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- High-temperature rearrangements of 2-acylisoxazol-5(2H)-ones and related oxazoles
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2-Acyl-3-arylisoxazol-5(2H)-ones give 2-alkyl(aryl)-4-aryloxazoles in good yields at 540°C under flash vacuum pyrolysis conditions, but at higher temperatures the expected oxazoles are accompanied by increasing amounts of isomeric 2,5-disubstituted oxazoles, as well as anilides and decomposition products of the 2,4-disubstituted oxazole. The rearrangement mechanisms have been studied by the use of 13C labelled substrates and p-substituted 3-arylisoxazolones. The 2,5-disubstituted oxazoles are considered to arise from 1H-azirines, and the anilides from the nitrone ketene isomer of the acylisoxazolone.
- Clark, Adrian D.,Ha, Uyen T.,Prager, Rolf H.,Smith, Jason A.
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p. 1029 - 1033
(2007/10/03)
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- Thermal Isomerizations of Substituted Benzyl Isocyanides: Relative Rates Controlled Entirely by Differences in Entropies of Activation
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The absolute and relative rates of thermal rearrangments of substituted benzyl isocyanides were obtained at the temperatures between 170 and 230 °C. The relative rates are independent of temperature and exhibit excellent Hammett correlations (p+ = -0.24). The temperature studies yielded activation parameters (ΔHY? and ΔSY?) and their differential counterparts (ΔΔHY-H? and ΔΔSY-H?). The differential terms were plotted against σ+. The secondary α-deuterium kinetic isotope effects (kD/kH = 1.11) were measured at several temperatures. The rate data can be rationalized with the cyclic TS. The substituent effects on the rates are due to the entropic contributions.
- Kim, Sung Soo,Choi, Won Jung,Zhu, Yu,Kim, Jin Hyun
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p. 1185 - 1189
(2007/10/03)
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- Using secondary α deuterium kinetic isotope effects to determine the symmetry of S(N)2 transition states
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The secondary α deuterium and heavy atom kinetic isotope effects found for two different S(N)2 reactions suggest that the magnitude of secondary α deuterium kinetic isotope effects can be determined by the length of only the shorter (stronger) reacting bond in an unsymmetrical S(N)2 transition state rather than by the usual nucleophile-leaving group distance. Although this means the interpretation of these isotope effects is more complex than has been recognized, the results suggest that they can be used to determine whether an S(N)2 transition state is symmetrical or unsymmetrical.
- Westaway, Kenneth Charles,Van Pham, Thuy,Fang, Yao-Ren
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p. 3670 - 3676
(2007/10/03)
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- Carboanion Reactivity: Kinetics of the Reactions of Benzyl Cyanide Anions with Aromatic Nitro-compounds
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Rate and equilibrium measurements are reported for the reactions in methanol of carbanions derived from 12 ring-substituted benzyl cyanides with 1,3,5-trinitrobenzene to give ?-adducts.Some data for reaction of the carbanions with 4-nitrobenzofuroxan were also measured.With increasing carbanion reactivity, rate constants approach a limit of just below 109 dm3 mol-1 s-1.Intrinsic reactivities of carbanions in ?-adduct forming reactions and in proton transfer reactions are compared.
- Atherton, John H.,Crampton, Michael R.,Duffield, Gaynor L.,Stevens, J. Andrew
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p. 443 - 448
(2007/10/02)
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- Degradation of 3-aryl-2-hydroxyiminopropionic acids into arylacetonitriles using 1,1'-carbonyldiimidazole or 2,2'-oxalyldi(o-sulfobenzimide)
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1,1'-Carbonyldiimidazole (1) is a useful reagent for the preparation of arylacetonitriles (9) from 3-aryl-2-hydroxyiminopropionic acids (8), and 2,2'-oxalyldi (o-sulfobenzimide) (2) can also be used for this purpose under essentially neutral conditions.
- Kitagawa,Kawaguchi,Inoue,Katayama
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p. 3030 - 3033
(2007/10/02)
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- Method of treating nausea and vomiting with certain substituted-phenylalkylamino (and aminoacid) derivatives and other serotonin depleting agents
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A method for the treatment of emesis in a mammal, which method comprises administering to said mammal an emesis inhibiting amount of a compound which depletes serotonin in the brain of mammals; among which are compounds having the formula: STR1 wherein, R is selected from hydrogen, loweralkyl, trifluoromethyl, carboxyl, or loweralkoxycarbonyl; R1 and R2 are hydrogen or loweralkyl; Z is trifluoromethyl or halogen; the optical isomers and pharmaceutically acceptable salts thereof; two of the preferred compounds of the invention are fenfluramine and norfenfluramine.
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- A Facile Synthesis of Nitriles from 1-Nitro-1-alkenes by Electroreduction
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Electroreduction of 1-nitro-1-alkenes in the presence of titanium(IV) chloride affords nitriles in good yields.This procedure provides a facile transformation of aldehydes to one-carbon elongated nitriles since the 1-nitro-1-alkenes are best prepared from aldehydes and nitromethane.
- Sera, Akira,Tani, Hiroyuki,Nishiguchi, Ikuzo,Hirashima, Tsuneaki
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p. 631 - 633
(2007/10/02)
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- Process for the preparation of substituted styrenes
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Substituted styrenes are prepared by treatment on N-acyl-B-phenethylamines with bases and removal by distillation of the styrene which is formed during the reaction.
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- PALLADIUM CATALYZED REACTION OF ARYL BROMIDES WITH CYANOMETHYLTRIBUTYLTIN. AROMATIC CYANOMETHYLATION
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Palladium catalyzed reaction of aryl bromides with cyanomethyltributyltin gave arylacetonitriles in moderate yields.Aryl bromides having strong electron-withdrawing groups (such as acyl, cyano, nitro, etc.) cannot be applied to the reaction.
- Kosugi, Masanori,Ishiguro, Masahiro,Negishi, Yoshikazu,Sano, Hiroshi,Migita, Toshihiko
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p. 1511 - 1512
(2007/10/02)
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