Highly efficient synthesis of C3-symmetric O-alkyl substituted triphenylenes and related Mannich derivatives†,Organic Chemistry Frontiers

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Highly efficient synthesis of C3-symmetric O-alkyl substituted triphenylenes and related Mannich derivatives†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2018-06-28 00:00:00 , DOI: 10.1039/c8qo00414e
Giacomo Berton _{1,

2,

3,

4} , Giuseppe Borsato _{1,

2,

3,

4} , Roberta Zangrando _{3,

4,

5,

6} , Andrea Gambaro _{2,

3,

4,

7,

8} , Fabrizio Fabris _{1,

2,

3,

4} , Alessandro Scarso _{1,

2,

3,

4}

Affiliation

C ₃-Symmetric tris-benzyl-O-substituted hexahydroxytriphenylene (HHTP) was prepared through selective ring opening with DIBAL-H in 48% yield (38% from HHTP in a two-step synthesis) avoiding the use of noxious, expensive and limited market availability reagents, with complete recovery of the undesired C_s co-product that is quantitatively recovered and converted back into HHTP. The C₃-symmetric triphenylene product was further functionalized through substitution, deprotection and Mannich condensation reactions affording a series of C₃-symmetric functionalized scaffolds in good yields for supramolecular applications.

中文翻译：

高效合成C ₃对称的O-烷基取代的三亚苯基和相关的曼尼希衍生物†

通过用DIBAL-H选择性开环制备C _3-对称的三-苄基-O-取代的六羟基联苯（HHTP），产率为48％（两步合成中HHTP为38％），避免了使用有毒，昂贵且受限制的物质市场上可买到的试剂，可以完全回收不需要的C _s副产物，并定量回收并转化回HHTP。通过取代，脱保护和曼尼希缩合反应将C ₃对称的三亚苯基产物进一步官能化，得到一系列C ₃对称的功能化支架，产量高，适用于超分子应用。

更新日期：2018-06-28

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