RUI: Synthesis of Heterohelicenes Using Acetylene-Activated SNAr Reactions

RUI：利用乙炔激活的 SNAr 反应合成杂螺烯

• 批准号: 1664549
• 负责人: Jeffrey Katz
• 金额: $ 22.78万
• 依托单位: Colby College
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2017
• 资助国家: 美国
• 起止时间: 2017-07-01 至 2021-06-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1664549&HistoricalAwards=false
• 关键词: RUI; Synthesis; Heterohelicenes; Using; Acetylene

The Chemical Synthesis Program of the Chemistry Division supports this project by Professor Jeffrey Katz, a faculty member in the Department of Chemistry at Colby College. He is investigating chemical methods that allow for the synthesis of chemical compounds called helicenes. Helicenes are unusual molecules that possess a rigid helical (screw-like) shape. The primary goal of the funded research is the development of technology that allows access to previously unknown helicenes containing nitrogen, oxygen, sulfur, and selenium atoms on terminal positions of the molecules. Compounds of this type have potential applications as chemical sensors, organic electronics, and new polymeric materials. Students working on this project are obtaining experience in organic chemical synthesis and materials chemistry. Professor Katz is highly active in the recruitment and retention of underrepresented minority students into chemistry and other scientific fields. He serves as co-Director of the Colby Achievement Program in the Sciences (CAPS), a summer bridge program at Colby College for entering first-year students from underrepresented backgrounds that fosters a climate of success and leadership within the minority student science population.Helicenes and their heteroaromatic variants are a promising compound class for use as chiral ligands, supramolecular building blocks, polymerization monomers, liquid crystals, optoelectronic materials, and components of molecular machines. A wide variety of [n]heterohelicenes are being accessed using acetylene-activated SNAr/anionic cyclization chemistry as the key diversifying transformation, a reaction cascade recently developed in the Katz laboratory. The cascade approach is efficient, highly modular, and allows for structural diversification at the final stages of the synthetic sequence. Further, the investigations target the production of non-racemic heterohelicenes through the use of chiral nucleophiles in the SNAr step of the cascade sequence, as well as adaptation of the method to produce heteroarene-terminated phenacenes. Undergraduate students working with Professor Katz travel to scientific conferences to present their research. Professor Katz leverages his attendance at these meetings by organizing and moderating Undergraduate Context Sessions, which support the educational environment for all attending undergraduate students. Such Sessions are included in the general programs of several major conferences in organic chemistry and have helped undergraduate students to become an increasingly recognized focus of the program structures.

化学部的化学合成计划支持这个项目由杰弗里·卡茨教授，在化学系的教员在科尔比学院。 他正在研究化学方法，以合成一种叫做螺旋烯的化合物。螺旋烯是具有刚性螺旋（螺旋状）形状的不寻常分子。资助研究的主要目标是开发技术，允许获得以前未知的螺旋烯，这些螺旋烯在分子的末端位置含有氮，氧，硫和硒原子。这类化合物在化学传感器、有机电子学和新型高分子材料等方面具有潜在的应用前景。参与该项目的学生将获得有机化学合成和材料化学方面的经验。Katz教授在招募和保留少数民族学生进入化学和其他科学领域方面非常活跃。他是科尔比科学成就计划（CAPS）的联合主任，这是科尔比学院的一个夏桥计划，旨在为来自代表性不足的背景的一年级学生提供入学机会，在少数学生科学人群中培养成功和领导力的氛围。螺旋烯及其杂芳变体是一种有前途的化合物类别，可用作手性配体，超分子构建块，聚合单体，液晶，光电材料和分子机器的组件。使用乙炔激活的SNAr/阴离子环化化学作为关键的多样化转化，正在获得各种各样的[n]杂螺烯，这是卡茨实验室最近开发的反应级联。级联方法是有效的，高度模块化的，并允许在合成序列的最后阶段的结构多样化。此外，调查的目标是通过使用手性亲核试剂在级联序列的SNAr步骤中生产非外消旋的杂螺烯，以及调整该方法以生产杂芳烃封端的非并苯。与Katz教授一起工作的本科生前往科学会议展示他们的研究。教授卡茨利用他在这些会议上出席组织和主持本科背景会议，支持所有参加本科生的教育环境。这些会议包括在有机化学的几个主要会议的一般程序，并帮助本科生成为程序结构的日益认可的焦点。

项目成果

Synthesis of chryseno[1,2-b]heteroarenes and phenanthro[1,2-b:8,7-b']diheteroarenes by an SNAr-anionic cyclization cascade reaction strategy

• DOI: 10.1016/j.tetlet.2020.152663
• 发表时间: 2020-11
• 期刊: Tetrahedron Letters
• 影响因子: 1.8
• 作者: James S Gilmore;D. Hwang;Jack M. Crissy;James M. Mercado-Rodríguez;J. L. Katz

Convergent Strategy for the Synthesis of Oxa-, Thia-, and Selena[5]helicenes by Acetylene-Activated S N Ar Reactions

乙炔激活 S N Ar 反应合成 Oxa-、Thia- 和 Selena[5]helicene 的收敛策略

• DOI: 10.1021/acs.joc.0c00052
• 发表时间: 2020
• 期刊: The Journal of Organic Chemistry
• 作者: Hoenig, Samuel M.;Yan, Youmian;Dougherty, Emily A.;Hudson, Reuben;Petovic, Sava;Lee, Christopher K.;Hu, Yusheng;Gomez, Lucas S.;Katz, Jeffrey L.
• 通讯作者: Katz, Jeffrey L.