TY - JOUR
T1 - Flow Synthesis of Triptycene via Triple Cycloaddition of Ynolate to Benzyne
AU - Iwata, Takayuki
AU - Yoshinaga, Tatsuro
AU - Shindo, Mitsuru
N1 - Funding Information:
This work was partially supported by the Japan Society for the Promotion of Science (JSPS KAKENHI, Grant No. JP18H02557, JP18H04418, JP18H04624, JP20H04780, JP17K14449, and JP20K15283), the NAGASE Science Technology Foundation (M.S.), the Asahi Glass Foundation (T.I.), the Qdai-jump Research Program Waka-ba Challenge at Kyushu University (T.I.), and the IRCCS Fusion Emergent Research Program (T.I.). This work was performed under the Cooperative Research Program ‘Network Joint Research Center for Materials and Devices’.JapanSocieyforhePomoionofScience(P18H02557JapanSocieyforhePromotionofScience(JP18H04418)JapanSocietyfrthePomoionofScience(JP18H04624JapanSocieyforhePomotonofScienceJP20H04780JapanSocietyforthePomotionofScienceJP17K14449JapanSocietyforthePomoionofScience(JP20K15283)NAGASEScienceTechnologyFoundation)Asahi GlasFoundaion)
Publisher Copyright:
© 2020 Georg Thieme Verlag. All rights reserved.
PY - 2020/12/1
Y1 - 2020/12/1
N2 - Flow synthesis of triptycene was achieved using triple cycloaddition of ynolate to benzyne. Employing the borate-type benzyne precursor, side reactions triggered by the addition of alkyllithium to benzyne were efficiently suppressed under microflow conditions, thus producing triptycene with a higher yield than that obtained under the corresponding batch conditions. Furthermore, ynolate prepared from α,α-dibromoester under microflow conditions was continuously added to the flow reaction with benzyne, which successfully synthesized triptycene in only one minute.
AB - Flow synthesis of triptycene was achieved using triple cycloaddition of ynolate to benzyne. Employing the borate-type benzyne precursor, side reactions triggered by the addition of alkyllithium to benzyne were efficiently suppressed under microflow conditions, thus producing triptycene with a higher yield than that obtained under the corresponding batch conditions. Furthermore, ynolate prepared from α,α-dibromoester under microflow conditions was continuously added to the flow reaction with benzyne, which successfully synthesized triptycene in only one minute.
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U2 - 10.1055/s-0040-1706417
DO - 10.1055/s-0040-1706417
M3 - Article
AN - SCOPUS:85090443826
SN - 0936-5214
VL - 31
SP - 1903
EP - 1906
JO - Synlett
JF - Synlett
IS - 19
ER -