TY - JOUR
T1 - Convenient Phenacene Synthesis by Sequentially Performed Wittig Reaction and Mallory Photocyclization Using Continuous-Flow Techniques
AU - Okamoto, Hideki
AU - Takahashi, Haruhiko
AU - Takane, Takamitsu
AU - Nishiyama, Yasuhiro
AU - Kakiuchi, Kiyomi
AU - Gohda, Shin
AU - Yamaji, Minoru
PY - 2017/7/3
Y1 - 2017/7/3
N2 - Various phenacenes possessing chrysene, picene, and fulminene frameworks were prepared by using a continuous-flow synthetic protocol in which Wittig reaction affording diarylethenes and their Mallory photocyclization producing phenacene skeletons were sequentially performed. The Wittig reaction solution, containing the diaryl ethene obtained from an arylaldehyde and an arylmethyltriphenylphosphonium salt, was mixed with an iodine solution in the flow system and, subsequently, the solution was subjected to the photoreaction. Desired phenacenes were obtained with high to moderate chemical yield. For the present protocol, isolation of the intermediary diarylethene, which is the key precursor of the phenacene, is unnecessary. The approach provides a convenient method to supply a variety of phenacene samples, which are needed for initial systematic surveys in material science.
AB - Various phenacenes possessing chrysene, picene, and fulminene frameworks were prepared by using a continuous-flow synthetic protocol in which Wittig reaction affording diarylethenes and their Mallory photocyclization producing phenacene skeletons were sequentially performed. The Wittig reaction solution, containing the diaryl ethene obtained from an arylaldehyde and an arylmethyltriphenylphosphonium salt, was mixed with an iodine solution in the flow system and, subsequently, the solution was subjected to the photoreaction. Desired phenacenes were obtained with high to moderate chemical yield. For the present protocol, isolation of the intermediary diarylethene, which is the key precursor of the phenacene, is unnecessary. The approach provides a convenient method to supply a variety of phenacene samples, which are needed for initial systematic surveys in material science.
KW - flow reaction
KW - Mallory photocyclization
KW - phenacene
KW - photochemistry
KW - Wittig reaction
UR - http://www.scopus.com/inward/record.url?scp=85018684520&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85018684520&partnerID=8YFLogxK
U2 - 10.1055/s-0036-1588775
DO - 10.1055/s-0036-1588775
M3 - Article
AN - SCOPUS:85018684520
VL - 49
SP - 2949
EP - 2957
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 13
ER -