Radical Germylzincation of Aryl- and Alkyl-Substituted Internal Alkynes
نویسندگان
چکیده
The stereoselective germylzincation of internal alkynes delivering trisubstituted vinylgermanes is achieved via a radical chain process involving Ph3GeH and Et2Zn with AIBN as initiator. Excellent levels regiocontrol are observed for non-symmetric (aryl, alkyl)-substituted alkynes, well propargylic alcohols aryl-, alkyl-, or silyl-substituted alkynes. reaction can be combined in one pot the Cu(I)-mediated electrophilic substitution C(sp 2)-Zn bond to obtain synthetically challenging tetrasubstituted vinylgermanes.
منابع مشابه
Highly selective synthesis of tetra-substituted furans and cyclopropenes: copper(I)-catalyzed formal cycloadditions of internal aryl alkynes and diazoacetates.
A convenient Cu(I)-catalyzed cycloaddition of electron rich internal aryl alkynes and diazoacetates was discovered for the chemoselective and regioselective synthesis of tetra-substituted furans and cyclopropenes in moderate isolated yields (18-67%), and alkyne conversion (29-73%).
متن کاملHighly regioselective synthesis of 2,4,5-(hetero)aryl substituted oxazoles by intermolecular [3+2]-cycloaddition of unsymmetrical internal alkynes.
A robust N-nucleophilic 1,3-N,O-dipole equivalent reacts with unsymmetrical internal alkynes under gold catalysis. Conjugation from a remote nitrogen lone pair enables and controls this convergent and highly regioselective process.
متن کاملPalladium-catalyzed three-component arylcyanation of internal alkynes with aryl bromides and K4[Fe(CN)6].
The one-pot, palladium-catalyzed, three-component coupling of aryl bromides, internal alkynes, and environmentally friendly K4[Fe(CN)6] provides an efficient and direct method for the preparation of beta-arylalkenylnitriles.
متن کاملSterically controlled diastereoselectivity in thio-Staudinger cycloadditions of alkyl/alkenyl/aryl-substituted thioketenes.
The [2 + 2] cycloadditions of thioketenes and imines are named as thio-Staudinger cycloadditions. The diastereoselectivity in thio-Staudinger cycloaddtions of alkyl/alkenyl/aryl-substituted thioketenes is rationalized. The steric effects of the thioketenes play an extremely important role in deciding the diastereoselectivity (cis/trans selectivity) through controlling exo- and endo-attack and s...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Organic Letters
سال: 2021
ISSN: ['1523-7060', '1523-7052']
DOI: https://doi.org/10.1021/acs.orglett.1c01367