Metalated N-heterocyclic reagents prepared by the frustrated Lewis pair TMPMgCl·BF3 and their addition to aromatic aldehydes and activated ketones.

نویسندگان

  • Sophia M Manolikakes
  • Milica Jaric
  • Konstantin Karaghiosoff
  • Paul Knochel
چکیده

Treatment of pyridines, quinoline and methylthiopyrazine with the frustrated Lewis pair TMPMgCl·BF(3) (1) leads to organotrifluoro borates which react readily with a variety of aromatic aldehydes in the absence of a transition metal catalyst.

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

Tandem nucleophilic addition-Oppenauer oxidation of aromatic aldehydes to aryl ketones with triorganoaluminium reagents.

In the presence of pinacolone, the in situ prepared triorganoaluminium reagents reacted with aromatic aldehydes to give ketones in moderate to high yield. We propose that the products are formed via a tandem organoaluminium reagents addition-Oppenauer oxidation sequence.

متن کامل

Expanding Water/Base Tolerant Frustrated Lewis Pair Chemistry to Alkylamines Enables Broad Scope Reductive Aminations

Lower Lewis acidity boranes demonstrate greater tolerance to combinations of water/strong Brønsted bases than B(C6 F5 )3 , this enables Si-H bond activation by a frustrated Lewis pair (FLP) mechanism to proceed in the presence of H2 O/alkylamines. Specifically, BPh3 has improved water tolerance in the presence of alkylamines as the Brønsted acidic adduct H2 O-BPh3 does not undergo irreversible ...

متن کامل

Thiazolium-derived N-heterocyclic carbene-catalyzed cross-coupling of aldehydes with unactivated imines.

Cross-coupling of aromatic aldehydes or benzoins with unactivated imines catalyzed by an N-heterocyclic carbene (NHC) affords alpha-amino ketones smoothly.

متن کامل

Application of a Polymer-Bound Thiazolium Salt to the Synthesis of Alpha-Hydroxy Ketones with an Aromatic and Aliphatic Substituent (Bencyloins) [1]

Alpha-Hydroxy ketones with an aromatic and aliphatic substituent were prepared with condensation of aromatic and aliphatic aldehydes in the presence of polymer-bound thiazolium salt.

متن کامل

Application of silica vanadic acid as a dual Lewis and Bronsted acid catalytic ability in Dakin West reaction

Silica Vanadic Acid, SVA, (oxo-vanadium has been supported on silica) as a dual Lewis and Bronsted acid ability was prepared and efficiently catalyzed one-pot multi-component condensation of enolizable ketones or alkyl acetoacetates with aromatic aldehydes, acetonitrile and acetyl chloride. The described reaction was produced β-acetamido ketone or ester derivatives in high to excellent yields i...

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 49 21  شماره 

صفحات  -

تاریخ انتشار 2013