107624-39-5Relevant articles and documents
Novel transformation of aryl 2-iodophenyl ketones into 1,3-diarylisoquinolines with (TMS)2NH, styrenes, NIS, and tBuOK
Shibasaki, Kaho,Togo, Hideo
, (2020/12/25)
Treatment of aryl 2-iodophenyl ketones with TMS2NH in the presence of Sc(OTf)3 at warming conditions, followed by the reaction with styrenes and NIS gave N-(1-aryl-2-iodoethyl) aryl 2-iodophenyl ketimines. Further treatment of N-(1-aryl-2-iodoethyl) aryl 2-iodophenyl ketimines with tBuOK in the presence of 1,10-phenanthroline at 120 °C generated 1,3-diarylisoquinolines in moderate yields through SET from tBuOK onto the iodophenyl group to form aryl radicals, their 6-endo-trig cyclization onto the vinyl groups, and aromatization of the cyclized intermediates. The present method is a novel approach for the preparation of the isoquinoline core via two steps from aryl 2-iodophenyl ketones.
Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[ b]naphthalene Derivatives
Li, Peng-Hua,Yu, Liu-Zhu,Zhang, Xiao-Yu,Shi, Min
supporting information, p. 4516 - 4520 (2018/08/09)
A Cu(I)-catalyzed coupling and cycloisomerization of diazo compounds with terminal yne-alkylidenecyclopropanes (ACPs) has been presented. This reaction starts from the formation of an allenic intermediate in the Cu(I)-catalyzed cross-coupling reaction of a diazo compound with terminal alkyne in yne-tethered ACP and then undergoes a domino cycloisomerization of a 6π-electrocyclization and cyclopropane ring-opening rearrangement to give functionalized cyclopenta[b]naphthalene derivatives in moderate to excellent yields under mild conditions.
One-pot synthesis of 4-methylisoquinolines via a sequential Pd-catalyzed Heck reaction and intramolecular cyclization
Tian, Yulin,Qi, Jianguo,Sun, Chenbin,Yin, Dali,Wang, Xiaojian,Xiao, Qiong
supporting information, p. 7262 - 7266 (2013/10/22)
An efficient, one-pot synthesis of 4-methylisoquinolines via a cascade Pd-catalyzed Heck reaction, intramolecular cyclization and isomerization has been developed. This reaction has a wide range of substrates with various functional groups, and the corresponding products have been obtained in good yields.
Synthesis of cyclic iodonium salts containing an asymmetric carbon atom
Tolstaya,Vanchikov,Vinnik,Asulyan
, p. 978 - 983 (2007/10/03)
We report the synthesis of two iodonium salts with an asymmetric carbon atom in the cation, viz. 3-methyl-10H,10-(4-tolyl)dibenz[b,e]iodinium tetrafluoroborate and the salt of the same cation with the anion of (-)-mono(N-α-phenylethyl)maleic acid amide as well as the synthesis of 3-methyl-10H-dibenz[b,e]-iodinium tetrafluoroborate. 1999 KluwerAcademic/Plenum Publishers.
Acylpalladation of internal alkynes and palladium-catalyzed carbonylation of (Z)-β-iodoenones and related derivatives producing γ-lactones and γ-lactams
Copéret, Christophe,Sugihara, Takumichi,Wu, Guangzhong,Shimoyama, Izumi,Negishi, Ei-Ichi
, p. 3422 - 3431 (2007/10/02)
The reaction of either an internal alkyne-organic halide mixture or (Z)-β-iodoenones with CO in the presence of a Pd-phosphine catalyst, e.g., Cl2Pd(PPh3)2, can give one of the three discrete types of compounds as the major products depending on the substrate structure and the reaction conditions. Those substrates which are convertible to (Z)-γ-oxo-α,β-unsaturated acylpalladium derivatives lacking δ-H atoms are converted to the corresponding 2-butenolides (13) in the presence of water, which serves as a H donor. Carbon monoxide most likely is the source of two electrons. Either in the absence of water (or any other suitable H source) or in the presence of some factors disfavoring the butenolide formation, the same reaction gives the corresponding dimeric product (16). Even in cases where there is an α-H atom in the α-substitutent, 1,4-elimination products (11), reported to be the major products in a related Pd-catalyzed reaction of terminal alkyne-aryl iodide mixtures with CO, were not detected. In sharp contrast, those substrates which can give rise to (Z)-γ-oxo-α,β-unsaturated acylpalladium derivatives containing δ-H atoms give, under comparable reaction conditions, enol lactones (12), i.e., (Z)-3-alkylidene-2-butenolides, contaminated with only very minor amounts of 22 even in cases where an excess (4 equiv) of water was present. The required (Z)-β-iodoenones can be readily prepared in one pot via ZrCp2-promoted cyclization of alkynes with nitriles. The ready availability of the starting compounds and the high Z stereoselectivity make the overall sequence an attractive synthetic route to 12. The courses of the Pd-catalyzed carbonylation reactions of (Z)-β-iodo-α,β-unsaturated imines 23 closely parallel the reactions of enones and produce the corresponding lactams, i.e., 24 and 25.
