17376-04-4Relevant articles and documents
A simple, efficient, and highly selective method for the iodination of alcohols using ZrCl4/NaI
Firouzabadi, Habib,Iranpoor, Nasser,Jafarpour, Maasoumeh
, p. 7451 - 7454 (2004)
Iodination of primary, secondary, allylic, and benzylic alcohols giving their corresponding iodides was achieved with ZrCl4/NaI in anhydrous CH3CN with excellent yields and selectivities.
Chiral organometallic reagents. Part XXIV.1 Iodine ate-complexes as intermediates in the iodine-lithium exchange reaction on 1,1-diiodoalkanes
Mueller, Michael,Stiasny, Hans-Christian,Broenstrup, Mark,Burton, Andrew,Hoffmann, Reinhard W.
, p. 731 - 736 (1999)
The iodine-lithium exchange reaction on the 1,1-diiodoalkanes 17 at -110 °C is initiated by the irreversible formation of yellow iodine ate-complexes, which are slowly transformed into the α-iodoalkyllithium compounds 21.
NEW PREPARATION OF ALKYL IODIDES FROM THE CORRESPONDING ALCOHOLS
Brunet, J. J.,Laurent, H.,Caubere, P.
, p. 5445 - 5446 (1985)
It is shown that alkyl iodides can be obtained from the corresponding alkyl α-chloroethyl carbonate and NaI or by direct reaction between the alcohol, α-chloroethyl chloroformate and NaI.
α-Iodoalkyl-iodine-ate complexes as observable intermediates in the iodine-magnesium exchange reaction
Schulze, Volker,Broenstrup, Mark,Boehm, Volker P. W.,Schwerdtfeger, Peter,Schimeczek, Michael,Hoffmann, Reinhard W.
, p. 824 - 826 (1998)
An intermediate with a half-life of 30 minutes has been observed in the iodine-magnesium exchange reaction of 1,1-diiodoalkanes in THF at -78°C. This intermediate is likely the ate complex 1. Its characteristic chemistry calls for a mechanistic reconsider
Rhodium-Catalyzed Regiodivergent Synthesis of Alkylboronates via Deoxygenative Hydroboration of Aryl Ketones: Mechanism and Origin of Selectivities
Zhang, Bing,Xu, Xin,Tao, Lei,Lin, Zhenyang,Zhao, Wanxiang
, p. 9495 - 9505 (2021/08/04)
Here, we report an efficient rhodium-catalyzed deoxygenative borylation of ketones to synthesize alkylboronates, in which the regioselectivity can be switched by the choice of the ligand. The linear alkylboronates were obtained exclusively in the presence of P(nBu)3, and PPh2Me favored the formation of branched alkylboronates. The protocol also allows access to 1,1,2-triboronates from the readily available ketones. Mechanistic studies suggest that this Rh-catalyzed deoxygenative borylation of ketones goes through an alkene intermediate, which undergoes regiodivergent hydroboration to afford linear and branched alkylboronates. The different steric effects of PPh2Me and P(nBu)3 were found to be responsible for product selectivity by density functional theory calculations. The alkene intermediate can alternatively undergo sequential dehydrogenative borylation and hydroboration to deliver the triboronates.
Direct Trifluoromethoxylation without OCF3-Carrier through In Situ Generation of Fluorophosgene
Donnard, Morgan,Guérin, Thomas,Hanquet, Gilles,Leroux, Frédéric R.,Panossian, Armen,Saiter, Jérémy
supporting information, p. 3139 - 3147 (2021/06/26)
Owing to the high interest in the OCF3 group for pharmaceutical and agrochemical applications, trifluoromethoxylation received great attention in the last years with several new methods for this approach towards OCF3-comprising compounds. Yet, it most often requires the beforehand preparation of specific F3CO? transfer reagents, which can be toxic, expensive, unstable, and/or generate undesired side-products upon consumption. To circumvent this, the in-situ generation of gaseous fluorophosgene from triphosgene, its conversion by fluoride into the OCF3 anion, and the direct use of the latter in nucleophilic substitutions is an appealing strategy, which, although recently approached, has not been fully exploited. We disclose herein our efforts towards this aim.
ANTIVIRAL TREATMENT
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Page/Page column 35, (2021/09/11)
The present description relates to the use of myramistin, its derivatives and the forms thereof for treating or ameliorating infections caused by enveloped viruses, methods for preparing the compounds and pharmaceutical compositions containing such compounds. In particular the use of myramistin, its derivatives and forms for treating or ameliorating infections caused by coronaviruses. More particularly, the present description relates to the use of myramistin, its derivatives and forms thereof for treating or ameliorating Coronavirus disease 2019 (COVID-19).
Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols
Chen, Yuming,He, Ru,Song, Hongjian,Yu, Guoqing,Li, Chenglin,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 1179 - 1183 (2021/02/01)
We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.
Copper-Catalyzed Regioselective Borocarbonylative Coupling of Unactivated Alkenes with Alkyl Halides: Synthesis of β-Boryl Ketones
Wu, Fu-Peng,Yuan, Yang,Schünemann, Claas,Kamer, Paul C. J.,Wu, Xiao-Feng
supporting information, p. 10451 - 10455 (2020/05/08)
The borocarbonylative coupling of unactivated alkenes with alkyl halides remains a challenge. In this communication, a Cu-catalyzed borocarbonylative coupling of unactivated alkenes with alkyl halides for the synthesis of β-boryl ketones has been developed. A broad range of β-boryl ketone derivatives was prepared in moderate to excellent yields with complete regioselectivity.
Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
Citarella, Andrea,Holzer, Wolfgang,Ielo, Laura,Langer, Thierry,Miele, Margherita,Pace, Vittorio,Urban, Ernst,Zehl, Martin
, p. 7629 - 7634 (2020/10/12)
The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.
