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Selenenate Anions (PhSeO − ) as Organocatalyst: Synthesis of trans ‐Stilbenes and a PPV Derivative
Author(s) -
Zheng Zhipeng,
Trofymchuk Oleksandra S.,
Kurogi Takashi,
Varela Elena,
Mindiola Daniel J.,
Walsh Patrick J.
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901201
Subject(s) - chemistry , dispersity , catalysis , derivative (finance) , halide , polymer chemistry , polymerization , coupling reaction , medicinal chemistry , organocatalysis , ion , polymer , organic chemistry , enantioselective synthesis , financial economics , economics
The selenenate anion (RSeO − ) is introduced as an active organocatalyst for the dehydrohalogen coupling of benzyl halides to form trans ‐stilbenes. It is shown that RSeO − is a more reactive catalyst than the previously reported sulfur analogues (sulfenate anion, RSO − ) and selenolate anions (RSe − ) in the aforementioned reaction. This catalytic system was also applied to the benzylic‐chloromethyl‐coupling polymerization (BCCP) of a bis‐chloromethyl arene to form ppv (poly(p‐phenylene vinylene))‐type polymers with high yields, M n (average molecular weight) up to 13,000 and Đ (dispersity) of 1.15.