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Synthesis of Soai Type 2‐Arylpyrimidine‐5‐carbaldehydes through Desulfurative Cross‐Coupling with Arylboronic Acids
Author(s) -
Maltsev Oleg V.,
Rausch Rodger,
Quan ZhengJun,
Hintermann Lukas
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403133
Subject(s) - chemistry , aryl , palladium , autocatalysis , yield (engineering) , condensation , pyrimidine , combinatorial chemistry , catalysis , stereochemistry , organic chemistry , alkyl , materials science , physics , metallurgy , thermodynamics
A two‐step synthesis of 2‐arylpyrimidine‐5‐carbaldehydes, which are of relevance as substrates for Soai's asymmetric autocatalysis, was realized by exploiting a hidden threefold symmetry in the target core structure. Condensation of Arnold's C 3 ‐symmetric vinamidinium cation with S ‐methylisothiouronium sulfate provides 2‐methylsulfanyl‐pyrimidine‐5‐carbaldehyde; introduction of aryl groups at C‐2 of the latter was accomplished by a Liebeskind–Srogl palladium‐catalyzed desulfurative (de‐methylsulfanylative) coupling with aryl boronic acids to obtain the target compounds 1 (14 examples, 60–95 % yield).