Thiophene synthesis via 1,1-carboboration.
نویسندگان
چکیده
Reaction of bis(tert-butylethynyl)sulfide with the boron Lewis acid reagents X-B(C6F5)2 (X = CH3, Cl, C6F5) in pentane at r.t. gave the respective borylated thiophenes in a sequence of 1,1-carboboration reactions. In contrast, bis(phenylethynyl)sulfide reacted with B(C6F5)3 only in a 2 : 1 molar ratio to give a benzothiophene derivative.
منابع مشابه
Intramolecular 1,1-carboboration versus intermolecular FLP addition in reactions of boranes and bis(phenylethynyl)telluroether.
Reactions of boranes with Te(CCPh)2 proceed via initial intermolecular 1,1-carboboration followed by either an intramolecular carboboration or an FLP addition to a second molecule of the intermediate, yielding 1-bora-4-tellurocyclohexa-2,5-diene heterocycles or tricylic derivatives of 1,4-ditellurocyclohexa-2,5-diene, respectively. The latter species is also shown to convert to the former upon ...
متن کاملPhosphirenium-borate zwitterion: formation in the 1,1-carboboration reaction of phosphinylalkynes.
Reaction of the acetylene Mes(2)P-C≡C-Ar with B(C(6)F(5))(3) at rt gives a zwitterionic phosphirenium product, which reacts further at >100 °C to complete the 1,1-carboboration reaction.
متن کاملAdvanced 1,1-carboboration reactions with pentafluorophenylboranes
The 1,1 carboboration reaction of a variety of metal-substituted alkynes with simple trialkylboranes R3B yields the respective alkenylboranes (Wrackmeyer reaction). The use of the strongly electrophilic R-B(C6F5)2 reagents allows for much milder reaction conditions and gives good yields of the respective bulky alkenylboranes from conventional terminal alkynes by means of 1,2-hydride migration. ...
متن کاملFacile synthesis of electrophilic vinyl boranes: reactions of alkynyl-borates and diazonium salts.
Reactions of alkynylborate salts, easily derived from reaction of frustrated Lewis pairs with terminal alkynes, with diazonium salts to induce 1,1-carboboration affording a facile and efficient route to substituted electrophilic vinyl boranes.
متن کاملUnusual product formation in a 1,1-carboboration reaction.
The reaction of the cross-conjugated enediyne Me2C[double bond, length as m-dash]C(C[triple bond, length as m-dash]CSiMe3)2 () with B(C6F5)3 gives the unusual borabicyclo[4.3.0]nonadiene product . The reaction sequence is initiated by 1,1-carboboration and is suggested to take a short subsequent sequence involving borane induced H migration reactions from the geminal pair of methyl groups.
متن کاملذخیره 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 ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 51 33 شماره
صفحات -
تاریخ انتشار 2015