Nickel-catalyzed Tishchenko reaction via hetero-nickelacycles by oxidative cyclization of aldehydes with nickel(0) complex.

نویسندگان

  • Sensuke Ogoshi
  • Yoichi Hoshimoto
  • Masato Ohashi
چکیده

A Ni(0)-catalyzed Tishchenko reaction which can be applied to a variety of aliphatic aldehydes (primary, secondary, tertiary) and aromatic aldehydes was developed. The reaction might proceed via a hetero-nickelacycle intermediate.

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

Nickel-Catalyzed Decarbonylation of Aromatic Aldehydes.

We report here the first systematic study of nickel-catalyzed decarbonylation of aromatic aldehydes under relatively mild conditions. Aldehydes with electron donating groups at para and ortho positions are generally successful with our method. For aldehydes with electron-withdrawing groups, significantly higher yields were achieved for ortho-substituted substrates than para ones, probably due t...

متن کامل

Nickel-catalyzed intermolecular alkyne insertion into cyclobutanones.

Cyclobutanones reacted with alkynes in the presence of nickel(0) catalysts to produce cyclohexenones. Oxidative cyclization of the carbonyl group of the cyclobutanone and the alkyne with the nickel(0) was followed by beta-carbon elimination from the resulting oxanickelacyclopentene and subsequent reductive elimination. This reaction achieves a formal alkyne insertion between the carbonyl carbon...

متن کامل

Nickeladihydrofuran. Key intermediate for nickel-catalyzed reaction of alkyne and aldehyde.

The formation of a nickeladihydrofuran by oxidative cyclization of an alkyne and an aldehyde with nickel(0) has been demonstrated; the transformation of the nickeladihydrofuran into an enone by decomposition, a lactone by carbonylation and an allylic alcohol by treatment with ZnMe(2) suggests that nickeladihydrofuran is an important key intermediate in a variety of catalytic reactions.

متن کامل

cis-stereoselective nickel-catalyzed cyclization/alkylation and arylation reactions of allenyl-aldehydes and -ketones with organozinc reagents.

Highly stereoselective alkylative and arylative cyclization reactions of allenyl-aldehydes and -ketones with organozinc reagents occur efficiently in the presence of catalytic Ni(COD)2 to afford cis-fused homoallylic cyclopentanols.

متن کامل

Nickel(0)-catalyzed intramolecular reductive coupling of alkenes and aldehydes or ketones with hydrosilanes.

A nickel(0)-catalyzed reductive coupling of aldehydes and simple alkenes with hydrosilanes has been developed. A variety of silyl-protected 1-indanol derivatives were prepared in a highly diastereoselective manner (up to >99 : 1 dr) by employing a combination of nickel(0)/N-heterocyclic carbene and triethylsilane. The present system was also applied to a reductive coupling with ketones. Prelimi...

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 46 19  شماره 

صفحات  -

تاریخ انتشار 2010