Iodine-catalyzed tandem synthesis of terminal acetals and glycol mono esters from olefins.
نویسندگان
چکیده
A new metal-free protocol is described for the synthesis of terminal acetals by tandem oxidative rearrangement of olefins using oxone as an oxidant in the presence of iodine. Moreover, a one-pot procedure for the preparation of glycol mono esters from olefins is also presented for the first time using the same reagent system.
منابع مشابه
Terminal olefins to linear α,β-unsaturated ketones: Pd(II)/hypervalent iodine co-catalyzed Wacker oxidation-dehydrogenation.
Development of a mild (35 °C, no Brønsted acids) tandem Wacker oxidation-dehydrogenation of terminal olefins was accomplished using palladium(II) and hypervalent iodine co-catalysis. The reaction affords linear aryl and alkyl α,β-unsaturated ketones directly from readily available terminal olefins in good yields (average 75% per step) with excellent functional group tolerance and chemo- and ste...
متن کاملPreparation of substituted enol derivatives from terminal alkynes and their synthetic utility.
Stereodefined enol derivatives of aldehydes are prepared from terminal alkynes. Specifically, terminal alkynes are known to undergo Cp2ZrCl2-catalyzed methylalumination. Here, we show that the resultant vinylalanes can be oxygenated with peroxyzinc species to generate trisubstituted enolates. Electrophilic trapping with carboxylic anydrides or silyl triflates yields trisubstituted enol esters o...
متن کاملDiastereoselective oxidative α-amination of aliphatic aldehydes catalyzed by iodine: synthesis of syn-γ-hydroxy-α-amino acetals.
Aldehydes can react with secondary amines to give α-amino acetals via the α-amination of aliphatic aldehydes catalyzed by iodine. The presence of an asymmetric hydroxylated center at the γ-position of the aldehyde was found to induce the stereoselective amino group. This method represents a stereoselective α-amination of γ-hydroxyaldehydes for the synthesis of syn-γ-hydroxy-α-amino acetals in g...
متن کاملCopper-catalyzed trifluoromethylation of internal olefinic C-H bonds: efficient routes to trifluoromethylated tetrasubstituted olefins and N-heterocycles.
The functionalization of internal olefins has been a challenging task in organic synthesis. Efficient CuII-catalyzed trifluoromethylation of internal olefins, that is, α-oxoketene dithioacetals, has been achieved by using Cu(OH)2 as a catalyst and TMSCF3 as a trifluoromethylating reagent. The push-pull effect from the polarized olefin substrates facilitates the internal olefinic C-H trifluorome...
متن کاملN-Sulfonylketenimines as Useful Synthons in a Novel Synthesis of Functionalized 2-Oxoindoline Derivatives
The synthesis of a novel class of 2-oxoindolin-3-ylidene-(1-arylhydrazinyl)-2-aryl(alkyl)ethylidene derivativesvia a copper-catalyzed tandem reaction of isatin, arylhydrazines, sulfonyl azides and terminal alkynes is described.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 49 17 شماره
صفحات -
تاریخ انتشار 2013