Gold(I)-catalysed [1,3] O→C rearrangement of allenyl ethers.

نویسندگان

  • Chandrababu Naidu Kona
  • Chepuri V Ramana
چکیده

A simple and rapid access to the α-substituted acryl aldehydes has been provided by developing a gold-catalysed [1,3] rearrangement of the allenyl ethers importantly with a record turnover frequency of 4600 h(-1) (at 0.05 mol% of the catalyst concentration) in homogeneous gold(I) catalysis.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Gold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers; synthesis of substituted 1,3-dienes.

Synthesis of substituted 1,3-dienes was achieved via gold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers. The N-heterocyclic carbene gold chloride catalyst (IPrAuCl) was superior in terms of activity and selectivity and afforded the 3,3-product in excellent yields. A proposed cation-π inter-action played a significant role in affecting the reaction rate.

متن کامل

Gold-catalyzed cyclization reactions of allenol and alkynol derivatives.

Although gold is chemically inert as a bulk metal, the landmark discovery that gold nanoparticles can be effective catalysts has opened up new and exciting research opportunities in the field. In recent years, there has been growth in the number of reactions catalyzed by gold complexes [gold(I) and gold(III)], usually as homogeneous catalysts, because they are soft Lewis acids. In addition, alk...

متن کامل

Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements

Gold-catalyzed intermolecular couplings of sulfonylacetylenes with allyl ethers are reported. A cooperative polarization of alkynes both by a gold catalyst and a sulfonyl substituent resulted in an efficient intermolecular tandem carboalkoxylation. Reactions of linear allyl ethers are consistent with the [3,3]-sigmatropic rearrangement mechanism, while those of branched allyl ethers provided [3...

متن کامل

Gold(I)-catalyzed propargyl Claisen rearrangement.

Homoallenic alcohols are prepared from propargyl vinyl ethers using a trinuclear gold(I)-oxo complex, [(Ph3PAu)3O]BF4, as a catalyst for propargyl Claisen rearrangement at room temperature. The gold(I)-catalyzed reaction is effective for a diverse collection of propargyl vinyl ethers, including substrates containing aryl and alkyl groups at the propargylic position, and hydrogen, aryl, and alky...

متن کامل

Towards the Ideal Synthesis of Homoallylic Ketones

Homoallylic ketones combine arguably two of the most synthetically useful functional groups in organic chemistry and are, therefore, very valuable synthetic intermediates. General methods for the synthesis of these intermediates include the allylation of carbonyl compounds via p-allyl palladium(II) complexes, the 1,4-addition of vinylmetal nucleophiles onto a,bunsaturated compounds, and the Cla...

متن کامل

ذخیره 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 نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Chemical communications

دوره 50 17  شماره 

صفحات  -

تاریخ انتشار 2014