Alkali Metal-Hydroxide-Catalyzed C(sp)-H Bond silylation.

نویسندگان

  • Anton A Toutov
  • Kerry N Betz
  • David P Schuman
  • Wen-Bo Liu
  • Alexey Fedorov
  • Brian M Stoltz
  • Robert H Grubbs
چکیده

Disclosed is a mild, scalable, and chemoselective catalytic cross-dehydrogenative C-H bond functionalization protocol for the construction of C(sp)-Si bonds in a single step. The scope of the alkyne and hydrosilane partners is substantial, providing an entry point into various organosilane building blocks and additionally enabling the discovery of a number of novel synthetic strategies. Remarkably, the optimal catalysts are NaOH and KOH.

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

Setting Cyclohexane Stereochemistry with Oxidation

Thanks to its atomand step-economy, C–H bond oxidation represents a “hot topic” in synthetic chemistry. However, due to the ubiquity of such bonds in organic molecules, regioand enantioselective C–H bond oxidation turns out to be extremely challenging, and efficient direct methods are in high demand. Compared to the success of aliphatic sp C–H oxidation by enzymes (such as cytochrome P450, Figu...

متن کامل

Copper-catalyzed oxidative C(sp3)–H/C(sp2)–H cross-coupling en route to carbocyclic rings† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc00250e Click here for additional data file.

The selective construction of C–C bonds, the essential link in organic molecules, in more efficient ways is always the central topic in synthetic chemistry. In the past several decades, transition-metal-catalyzed C–C bond construction via the activation of ubiquitous C–H bonds has attracted increasing attention, due to the atom and step economy. While the recent fast developments in this area o...

متن کامل

Ionic and Neutral Mechanisms for C-H Bond Silylation of Aromatic Heterocycles Catalyzed by Potassium tert-Butoxide.

Exploiting C-H bond activation is difficult, although some success has been achieved using precious metal catalysts. Recently, it was reported that C-H bonds in aromatic heterocycles were converted to C-Si bonds by reaction with hydrosilanes under the catalytic action of potassium tert-butoxide alone. The use of Earth-abundant potassium cation as a catalyst for C-H bond functionalization seems ...

متن کامل

Reusable ionic liquid-catalyzed oxidative coupling of azoles and benzylic compounds via sp(3) C-N bond formation under metal-free conditions.

The heterocyclic ionic liquid-catalyzed direct oxidative amination of benzylic sp(3) C-H bonds via intermolecular sp(3) C-N bond formation for the synthesis of N-alkylated azoles under metal-free conditions is reported for the first time. The catalyst 1-butylpyridinium iodide can be recycled and reused with similar efficacies for at least eight cycles.

متن کامل

Manganese-catalyzed allylation via sequential C–H and C–C/C–Het bond activation† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc00230k Click here for additional data file.

Manganese-catalyzed sequential C–H and C–C/C–Het bond activation to synthesize allylic alcohols, allylated arenes, functionalized cyclopentenes and skipped dienes is reported. This protocol can be readily scaled up and various coupling partners are applied in manganese catalysis for the first time. Moreover, manganese-catalyzed alkenyl C(sp)–H activation is also shown. Complimentary to the stan...

متن کامل

ذخیره در منابع من

ذخیره در منابع من قبلا به منابع من ذحیره شده

{@ msg_add @}


  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:
  • Journal of the American Chemical Society

دوره 139 4  شماره 

صفحات  -

تاریخ انتشار 2017