TY - JOUR
T1 - Regioselective One-Pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates
AU - Umezu, Satoshi
AU - dos Passos Gomes, Gabriel
AU - Yoshinaga, Tatsuro
AU - Sakae, Mikei
AU - Matsumoto, Kenji
AU - Iwata, Takayuki
AU - Alabugin, Igor
AU - Shindo, Mitsuru
N1 - Funding Information:
We thank T. Matsumoto at Kyushu University for the X-ray crystal structure analyses. This work was partially supported by JSPS KAKENHI Grant Number (No. JP16H01157, No. JP26293004), Science and Technology Research Promotion Program for Agriculture, forestry, fisheries and food industry (M.S.), the Asahi Glass Foundation (K.M.), and the Cooperative Research Program of the Network Joint Research Center for Materials and Devices. I.A. is grateful to the National Science Foundation for support (CHE-1152491) and NSF XSEDE (TG-CHE160006) and FSU RCC for computational resources. G.d.P.G. thanks IBM for its 2016 Ph.D. Scholarship.
Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2017/1/24
Y1 - 2017/1/24
N2 - We developed the novel one-pot synthetic method of substituted triptycenes by the reaction of ynolates and arynes. This four-step process involves three cycloadditions and electrocyclic ring opening of the strained Dewar anthracene. Each of the three related but structurally distinct classes of nucleophiles (ynolate, enolate, and anthracenolate) reacts with o-benzyne in the same predictable manner controlled by chelation and negative hyperconjugation. The resulting functionalized C3-symmetrical triptycenes hold promise in the design of functional materials.
AB - We developed the novel one-pot synthetic method of substituted triptycenes by the reaction of ynolates and arynes. This four-step process involves three cycloadditions and electrocyclic ring opening of the strained Dewar anthracene. Each of the three related but structurally distinct classes of nucleophiles (ynolate, enolate, and anthracenolate) reacts with o-benzyne in the same predictable manner controlled by chelation and negative hyperconjugation. The resulting functionalized C3-symmetrical triptycenes hold promise in the design of functional materials.
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U2 - 10.1002/anie.201609111
DO - 10.1002/anie.201609111
M3 - Article
C2 - 28029205
AN - SCOPUS:85009761272
SN - 1433-7851
VL - 56
SP - 1298
EP - 1302
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 5
ER -