- Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene
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The use of vinyl electrophiles in synthesis has been hampered by the lack of access to a suitable reagent that is practical and of appropriate reactivity. In this work we introduce a vinyl thianthrenium salt as an effective vinylating reagent. The bench-stable, crystalline reagent can be readily prepared from ethylene gas at atmospheric pressure in one step and is broadly useful in the annulation chemistry of (hetero)cycles, N-vinylation of heterocyclic compounds, and palladium-catalyzed cross-coupling reactions. The structural features of the thianthrene core enable a distinct synthesis and reactivity profile, unprecedented for other vinyl sulfonium derivatives.
- Juliá, Fabio,Paulus, Fritz,Ritter, Tobias,Yan, Jiyao
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supporting information
p. 12992 - 12998
(2021/09/03)
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- Pd/Cu-Catalyzed Vinylation of Terminal Alkynes with (2-Bromoethyl)diphenylsulfonium Triflate
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The potential of (2-bromoethyl)diphenylsulfonium triflate to be a powerful vinylation reagent was determined by the Sonogashira cross-coupling reactions with terminal alkynes. The vinylation proceeded smoothly at 25 °C under Pd/Cu catalysis to afford a variety of 1- and 2-unsubstituted 1,3-enynes in moderate to excellent yields. This protocol represents the first application of (2-haloethyl)diphenylsulfonium triflate as a CH═CH2 transfer source in organic synthesis.
- Ming, Xiao-Xia,Wu, Shuai,Tian, Ze-Yu,Song, Jia-Wei,Zhang, Cheng-Pan
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supporting information
p. 6795 - 6800
(2021/09/08)
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- Annulation of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts: Synthesis of dihydrofuran derivatives
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A new synthetic approach to dihydrofuran derivatives via the annulation reaction of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts has been developed. A variety of dihydrofuran derivatives were prepared in moderate to good yields under mild conditions. The products could be readily transformed to the corresponding furans via the dehydrogenation with DDQ.
- Chen, Zi-Cong,Tong, Lang,Du, Zhi-Bo,Mao, Zhi-Feng,Zhang, Xue-Jing,Zou, Yong,Yan, Ming
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supporting information
p. 2634 - 2638
(2018/04/26)
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- Salts and crystals of EGFR (epidermal growth factor receptor) inhibitor and their preparation methods
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The invention discloses salts and crystals of an EGFR (epidermal growth factor receptor) inhibitor and their preparation methods, as well as application of the salts and crystals in preparation of drugs to treat non-small cell lung cancer.
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Paragraph 0098; 0101; 0102
(2018/05/16)
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- A convenient cyclopropanation process of oxindoles via bromoethylsulfonium salt
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A practical convenient conversion of oxindoles into the corresponding spirocyclopropyl oxindoles is achieved efficiently using bromoethylsulfonium salt, which is easily prepared on a large scale and is stable crystalline. This reaction of bromoethylsulfonium salt with different substituted unprotected oxindoles proceeded under mild condition and provided moderate yields.
- Qin, Hui,Miao, Yuanyuan,Zhang, Ke,Xu, Jian,Sun, Haopeng,Liu, Wenyuan,Feng, Feng,Qu, Wei
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p. 6809 - 6814
(2018/10/20)
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- FUSED-RING OR TRICYCLIC ARYL PYRIMIDINE COMPOUND USED AS KINASE INHIBITOR
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Disclosed is a fused-ring or tricyclic aryl pyrimidine compound used as a mutation selectivity EGFR inhibitor. Specifically, disclosed is a compound represented by formula (I) and used as an EGFR inhibitor or a pharmaceutically acceptable salt thereof.
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Paragraph 0286; 0289; 0290
(2018/03/25)
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- An efficient method for the synthesis of 2′,3′-nonsubstituted cycloalkane-1,3-dione-2-spirocyclopropanes using (2-bromoethyl)-diphenylsulfonium trifluoromethanesulfonate
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An efficient and practical synthesis of 2′,3′-nonsubstituted cyclohexane-1,3-dione-2-spirocyclopropanes using a sulfonium salt was achieved. The reaction of 1,3-cyclohexanediones and (2-bromoethyl)diphenylsulfonium trifluoromethanesulfonate with powdered K2CO3 in EtOAc at room temperature (r.t.) provided the corresponding spirocyclopropanes in high yields. The synthetic method was also applied to 1,3-cyclopentanedione, 1,3-cycloheptanedione, 1,3-indanedione, acyclic 1,3-diones, ethyl acetoacetate, and Meldrum's acid.
- Nambu, Hisanori,Ono, Naoki,Hirota, Wataru,Fukumoto, Masahiro,Yakura, Takayuki
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p. 1763 - 1768
(2016/12/09)
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- Remote chiral induction in vinyl sulfonium salt-mediated ring expansion of hemiaminals into epoxide-fused azepines
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The planet of the azepines: Epoxy-fused azepines have been synthesized in a highly selective reaction with hemiaminals and vinyl sulfonium salts. Stereochemistry is controlled by the substituent at the four- or five-position of the hemiaminal. The key step involves ring-opening of the hemiaminal, conjugate addition onto a vinyl sulfonium salt, and epoxidation of the aldehyde by the in situ formed sulfur ylide. Copyright
- Yar, Muhammad,Unthank, Matthew G.,McGarrigle, Eoghan M.,Aggarwal, Varinder K.
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supporting information; experimental part
p. 372 - 375
(2011/10/09)
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- Bromoethylsulfonium salt-a more effective annulation agent for the synthesis of 6- and 7-membered 1,4-heterocyclic compounds
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(Chemical Equation Presented) Reaction of bromoethylsulfonium salt with 1,2-/1,3-aminoalcohols gave six- and seven-membered rings in good-to-excellent yields. The reactions proceed through generation of a vinyl sulfonium salt followed by annulation to give 1,4-heterocyclic compounds such as morpholines and benzoxazepines in a simple procedure. The method accommodates a range of nitrogen substituents and the amino alcohol can be substituted by amino thiols and diamines to give thiomorpholines, piperazines and benzodiazepines.
- Yar, Muhammad,McGarrigle, Eoghan M.,Aggarwal, Varinder K.
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supporting information; experimental part
p. 257 - 260
(2009/08/08)
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- THIENO-PYRIDINE DERIVATIVES AS MEK INHIBITORS
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A series of thieno[2,3-6]pyridine derivatives, attached at the 2-position to a substituted anilino moiety, which are substituted in the 3-position by a carbonyl group linked to a pyrrolidin-1-yl ring which in turn forms part of a heteroatom-containing fus
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Page/Page column 63
(2010/01/12)
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- An annulation reaction for the synthesis of morpholines, thiomorpholines, and piperazines from β-heteroatom amino compounds and vinyl sulfonium salts
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(Chemical Equation Presented) Heterocycling: Diphenyl vinyl sulfonium salt 1 acts first as an electrophile, then a base, and then again as an electrophile in this operationally simple, high yielding, one-pot synthesis of pharmacologically important morpholines, thiomorpholines, and piperazines. Compound 1 is an excellent synthon for the 1,2-ethane dication.
- Yar, Muhammad,McGarrigle, Eoghan M.,Aggarwal, Varinder K.
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p. 3784 - 3786
(2008/12/23)
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- Epoxy-annulations by reactions of α-amido ketones with vinyl sulfonium salts. Reagent versus substrate control and kinetic resolution
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(Chemical Equation Presented) Diphenyl vinyl sulfonium salt and chiral amido-ketones undergo highly diastereoselective epoxy-annulation reactions in good yield. The use of a chiral vinyl sulfonium salt dominates the stereochemical outcome of the annulatio
- Unthank, Matthew G.,Tavassoli, Bahareh,Aggarwal, Varinder K.
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supporting information; experimental part
p. 1501 - 1504
(2009/04/12)
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- The use of vinyl sulfonium salts in the stereo-controlled asymmetric synthesis of epoxide- and aziridine-fused heterocycles: Application to the synthesis of (-)-balanol
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(Chemical Equation Presented) Lift your ylides: An asymmetric, epoxy-annulation reaction mediated by a vinyl sulfonium salt converts aminoaldehydes and -ketones into fused heterocyclic epoxides. The methodology was extended to an aziridine-annulation reac
- Unthank, Matthew G.,Hussain, Nigel,Aggarwal, Varinder K.
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p. 7066 - 7069
(2007/10/03)
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- A new method for the preparation of nitrogen-containingheterocycles using diphenylsulfonium triflates
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Various nitrogen heterocycles were produced by the reactions of ω-bromoalkyldiphenylsulfonium or diphenylsyylsulfonium triflates with nitrogen nucleophiles. Further, the reactions of diphenylstyrylsulfonium triflates with N-metalated phthalimide and imida
- Yamanaka, Hiroyuki,Yamane, Yoshinobu,Mukaiyama, Teruaki
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p. 2813 - 2826
(2007/10/03)
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- Reactivity and rearrangements of dialkyl- and diarylvinylsulfonium salts with indole-2- and pyrrole-2-carboxaldehydes
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Various dialkyl- and diarylvinylsulfonium salts react with indole-2- carboxaldehydes in the presence of sodium hydride and sodium azide to form tricyclic azido alcohols analogous to 2. With pyrrole-2-carboxaldehyde, [2,3] sigmatropic and other rearrangeme
- Wang, Yufeng,Zhang, Weihong,Colandrea, Vincent J.,Jimenez, Leslie S.
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p. 10659 - 10672
(2007/10/03)
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