Stille couplings catalytic in tin: a "Sn-F" approach.

نویسندگان

  • R E Maleczka
  • W P Gallagher
چکیده

A new tin recycling method for Stille couplings catalytic in tin is reported. PMHS made hypercoordinate by KF((aq)) allows Me(3)SnH to be efficiently recycled during a Pd(0)-catalyzed hydrostannation/Stille cascade. Relative to previously disclosed protocols, reaction times are shorter and because this process is believed to proceed through a Me(3)SnF intermediate the hazards and problems associated with trimethyltins are also diminished.[reaction: see text]

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

Stille couplings catalytic in tin: the "Sn-O" approach.

A one-pot tandem Pd-catalyzed hydrostannylation/Stille coupling protocol for the stereoselective generation of vinyltins and their subsequent union, employing only catalytic amounts of tin, is described. By recycling the organotin halide Stille byproduct back to organotin hydride, a hydrostannylation/cross-coupling sequence can be carried out with catalytic amounts of tin. Such a process is mos...

متن کامل

Stille reactions catalytic in tin: a "Sn-F" route for intermolecular and intramolecular couplings.

Polymethylhydrosiloxane (PMHS) made hypercoordinate by KF(aq) allows Me(3)SnH to be recycled during a Pd(0)-catalyzed hydrostannation/Stille cascade. Starting with a variety of alkynes, in situ vinyltin formation is followed by Stille reaction with aryl, styryl, benzyl, or vinyl electrophiles present in the reaction mixture. Both inter- and intramolecular versions of the process are possible wi...

متن کامل

Versatile asymmetric synthesis of the kavalactones: first synthesis of (+)-kavain.

[reaction: see text] Three asymmetric pathways to the kavalactones have been developed. The first method is chiral auxiliary-based and utilizes aldol reactions of N-acetyl thiazolidinethiones followed by a malonate displacement/decarboxylation reaction. The second approach uses the asymmetric catalytic Mukaiyama additions of dienolate nucleophile equivalents developed by Carreira and Sato. Fina...

متن کامل

Regularities of solid-phase interaction of tin and molybdenum oxides: Catalytic properties

The interaction in the system of SnO2 and h-MoO3 prepared by their joint mechanical activation in a roller-ring vibratory mill was investigated. A series of catalysts was prepared with SnO2: h-MoO3 molar ratio 1:1; 1:2.3; 2.3:1 and 5.7:1. The catalysts were characterized by various techniques including X-ray phase, X-ray diffraction (XRD) and synchron...

متن کامل

Elements of regiocontrol in palladium-catalyzed oxidative arene cross-coupling.

An increasing emphasis on waste minimization has prompted research aimed at replacing common synthetic techniques with greener alternatives. In biaryl synthesis, direct arylation1,2 is an emerging alternative to Suzuki and Stille couplings;3 however, a more efficient strategy would involve the direct catalytic crosscoupling of two arenes without recourse to stoichiometric activating groups (eq ...

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:
  • Organic letters

دوره 3 26  شماره 

صفحات  -

تاریخ انتشار 2001