Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides.

نویسندگان

  • Tingting Fu
  • Hongwei Qiao
  • Zhimin Peng
  • Gaobo Hu
  • Xueji Wu
  • Yuxing Gao
  • Yufen Zhao
چکیده

We present a novel and highly efficient methodology that allows for the construction of C-P bonds via the palladium-catalyzed air-based oxidative coupling of various commercially available arylboronic acids with easily oxidized H-phosphine oxides leading to valuable aryl phosphine oxides, particularly triarylphosphine oxides, with the use of air as the green oxidant, broad substrate applicability and good to excellent yields. The described catalytic system should be an efficient complement to the Chan-Lam type reaction and be useful in synthetic programs.

برای دانلود رایگان 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

Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides.

Herein an efficient and direct copper-catalyzed coupling of oxazoline-containing aryl bromides with electron-deficient secondary phosphine oxides is reported. The resulting tertiary phosphine oxides can be reduced to prepare a range of PHOX ligands. The presented strategy is a useful alternative to known methods for constructing PHOX derivatives.

متن کامل

Palladium(II)-catalyzed Heck reaction of aryl halides and arylboronic acids with olefins under mild conditions

A series of general and selective Pd(II)-catalyzed Heck reactions were investigated under mild reaction conditions. The first protocol has been developed employing an imidazole-based secondary phosphine oxide (SPO) ligated palladium complex (6) as a precatalyst. The catalytic coupling of aryl halides and olefins led to the formation of the corresponding coupled products in excellent yields. A v...

متن کامل

An air stable and efficient palladium catalyst for Suzuki-Miyaura cross coupling reaction at room temperature

The cross-coupling reaction between phenylboronic acid and various types of aryl halides (Suzuki reaction) was carried out using a catalytic amount of a new palladium catalyst (1-benzyl-3-(1-benzyl-1-methylpyrrolidin-1-ium-2-yl) pyridin-1-ium palladium chloride [DBNT][PdCl4]) in poly (ethylene glycol) (PEG-200) in the presence of KOH as the base. This new catalyst was synthesized and...

متن کامل

An air stable and efficient palladium catalyst for Suzuki-Miyaura cross coupling reaction at room temperature

The cross-coupling reaction between phenylboronic acid and various types of aryl halides (Suzuki reaction) was carried out using a catalytic amount of a new palladium catalyst (1-benzyl-3-(1-benzyl-1-methylpyrrolidin-1-ium-2-yl) pyridin-1-ium palladium chloride [DBNT][PdCl4]) in poly (ethylene glycol) (PEG-200) in the presence of KOH as the base. This new catalyst was synthesized and...

متن کامل

Aerobic addition of secondary phosphine oxides to vinyl sulfides: a shortcut to 1-hydroxy-2-(organosulfanyl)ethyl(diorganyl)phosphine oxides

Secondary phosphine oxides react with vinyl sulfides (both alkyl- and aryl-substituted sulfides) under aerobic and solvent-free conditions (80 °C, air, 7-30 h) to afford 1-hydroxy-2-(organosulfanyl)ethyl(diorganyl)phosphine oxides in 70-93% yields.

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

عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 12 18  شماره 

صفحات  -

تاریخ انتشار 2014