Xi:Irritant;
591-50-4Relevant articles and documents
Flood, E. A.,Horvitz, L.
, p. 2534 - 2539 (1933)
Hunter,B.K.,Reeves,L.W.
, p. 1399 - 1414 (1968)
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Whitmore,Thorpe
, p. 782,783 (1933)
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Gold-catalyzed synthesis of iodofulvenes
Noesel, Pascal,Lauterbach, Tobias,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
, p. 8634 - 8641 (2013)
We report the gold-catalyzed synthesis of highly functionalized iodofulvenes from iododialkynes under mild conditions. The catalytic cycle involves the formation of gold acetylides and vinylgold intermediates. These intermediates can then undergo an unprecedented iodine/gold exchange. This new pathway for catalyst transfer in dual gold catalysis opens up the possibility of highly regioselective transformations directed by the gold in the organogold intermediates. The resulting products are well suited for further metal-mediated coupling reactions, allowing the synthesis of extended π-systems. Iodine/gold exchange: A gold-catalyzed iodine transfer allows the efficient synthesis of benzofulvenes with iodo substituents on the fulvene core (see scheme). The new dual-activation catalysts are efficient catalysts for this new type of cycloisomerization. Copyright
(Diacetoxyiodo)benzene-Mediated Transition-Metal-Free Amination of C(sp3)-H Bonds Adjacent to Heteroatoms with Azoles: Synthesis of N-Alkylated Azoles
Sun, Bin,Yan, Zhiyang,Jin, Can,Su, Weike
, p. 2432 - 2436 (2018)
A novel PhI(OAc) 2 -mediated cross-dehydrogenative coupling reaction of α-C(sp 3)-H bonds adjacent to a hetero atom with various azoles has been developed, which provides an alternative method for constructing C-N bonds with high atom efficiency. This new protocol requires no metal catalyst and it provides ready access to a wide range of N-alkylated azole derivatives in moderate to excellent yields by using commercially available PhI(OAc) 2 as the sole oxidant. Furthermore, the method is effective on a gram scale, which highlights the practicality of this transformation. The result of radical-captured experiments indicated that the transformation might involve a free-radical pathway.
Functionalized Nitrogen Atom Transfer Catalyzed by Cytochrome P-450
Svastits, Edmund W.,Dawson, John H.,Breslow, Ronald,Gellman, Samuel H.
, p. 6427 - 6428 (1985)
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Preparation of Bis(arylthio)iodobenzene and Reaction with 1-Alkynes. A Novel Route to 1,2-Bis(arylthio)alkenes
Kita, Yasuyuki,Okuno, Takayuki,Tohma, Hirofumi,Akai, Shuji,Matsumoto, Keita
, p. 2717 - 2720 (1994)
The in situ reaction of a novel hypervalent iodine reagent 2b having an arylthio ligand, prepared from phenyliodine diacetate and 2,3,5,6-tetrafluorothiophenol 1b in pyridine, with 1-alkynes 3 gave 1,2-bis(arylthio)alkenes 4 in good yields.
Silbert et al.
, p. 3670 (1968)
Inversion of Configuration in Nucleophilic Vinylic Substitutions of (E)-β-Alkylvinyliodonium Tetrafluoroborates with Halides
Ochiai, Masahito,Oshima, Kunio,Masaki, Yukio
, p. 7059 - 7061 (1991)
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Syntheses of (1,1-Dihydroperfluoroalkyl)aryliodonium Triflates and Their Analogues
Unemoto, Teruo,Gotoh, Yoshihiko
, p. 235 - 240 (1985)
(1,1-Dihydroperfluoroalkyl)phenyl- and -p-fluorophenyliodonium triflates 2 and 3 were synthesized by the reaction of 1-bis(trifluoroacetoxy)iodo-1,1-dihydroperfluoroalkanes 1 with triflic acid and benzene or fluorobenzene in 1,1,2-trichloro-trifluoroethane.The use of fluorosulfonic acid and sulfuric acid instead of triflic acid afforded (1,1-dihydroperfluoroalkyl)phenyliodonium fluorosulfonate 4 and sulfate 5, respectively.Similarly, (1,1,ω-trihydroperfluoroalkyl)phenyliodonium triflate 7 and 1,1,5,5-tetrahydroperfluoropentane-1,5-bisphenyliodonium triflate 9 were synthesized.
Reverse Halogenation Using Supported Copper(I) Iodide
Clark, James H.,Jones, Craig W.
, p. 1409 - 1410 (1987)
Alumina and charcoal supported copper(I) iodide reagents can be used to convert bromo- and chloro-benzenes into iodobenzenes with no back attack by bromide or chloride.
Milas, N. A.,Surgenor, D. M.
, p. 205 - 208 (1946)
The [closo-B12H11-1-IAr]- zwitterion as a precursor to monosubstituted derivatives of [closo-B12H12]2-
Tokarz, Pawe?,Kaszyński, Piotr,Domaga?a, S?awomir,Wo?niak, Krzysztof
, p. 70 - 79 (2015)
Reactions of [closo-B12H12]2- with ArI(OAc)2 in aqueous AcOH in the presence of [NEt4]+ or [NHEt3]+ give [closo-B12H11-1-IAr]- (1) in 74-95% yield as a white precipitate. The zwitterions decompose in CD3CN solutions with rates k = 3.30 ± 0.04 × 10-4 s-1 (Ar = Ph, 1a[NEt4]) and k = 1.96 ± 0.01 × 10-4 s-1 (Ar = C6H4OMe-4, 1b[NEt4]) at 0 °C. Reactions of the zwitterion with Me2NCHS and pyridine gave the corresponding products [closo-B12H11-1-SCHNMe2]- (2) and [closo-B12H11-1-NC5H5]- (3) isolated in 25-27% and up to 44% yield, respectively. The former anion is a protected thiol derivative, which was transformed to the sulfonium derivative [closo-B12H11-1-S(CH2)5]- (8). The molecular structure and spectroscopic properties of pyridinium zwitterion 3 were analyzed experimentally and computationally (B3LYP), and results compared with those for the [closo-B10H9-1-NC5H5]- (4) analog. Mechanisms of formation of 2-4 from appropriate aryliodonium zwitterions were analyzed with the M062x computational method.
Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes
Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
supporting information, (2021/05/26)
Owing to both Lewis and Bronsted acid active sites on sulfated polyborate under homogenous conditions, we were keen on developing iodination protocol of arenes that can meet the requirement of regioselectivity and higher yield. The sulfated polyborate activates N-iodosuccinimide for mono iodination of highly activated substrates viz. phenols, anilines under anhydrous condition. Water tunes sulfated polyborate to generate more Bronsted acid sites resulting in rapid activation of NIS for diiodination. The protocol was equally applicable to diiodination of 4-hydroxyphenylacetic acid to synthesize 4-hydroxy-3,5-diiodophenylacetic acid, an intermediate of tiratricol, a thyroid treatment drug. This protocol was further integrated via one-pot sequential iodination and Sonogashira coupling to synthesize aryl acetylenes, building blocks for the synthesis of a variety of specialty chemicals, API, and natural products.
A convenient synthetic approach to a novel class of aryldifluoromethyl pyrimidine derivatives containing strobilurin motif as insecticidal agents
Cai, Zengfei,Cao, Yangyang,Du, Xiaohua,Hao, Shulin,Zhang, Wenliang
supporting information, (2021/10/07)
A series of aryldifluoromethyl pyrimidine compounds containing strobilurin were synthesized through bioelectronic isometric design with azoxystrobin as the lead compound and a convenient approach to aryldifluoromethylpyrimidine intermediates was developed, which features mild reaction conditions and simple operation. The title compounds and aryldifluoromethylpyrimidine intermediates were characterized by NMR and HRMS. Both 7c and 7l of the preliminary screening tests showed 100% inhibition against Mythimna separata at 100 mg/L. At 20 mg/L, the lethal rate of 7l against Mythimna separata can be up to 80%.
