CAREER: SusChEM: New Methods for Cu-Catalyzed Cross-Coupling Reactions

职业：SusChEM：铜催化交叉偶联反应的新方法

• 批准号: 1554760
• 负责人: Michael Brown
• 金额: $ 67.5万
• 依托单位: Indiana University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2016
• 资助国家: 美国
• 起止时间: 2016-04-01 至 2022-05-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1554760&HistoricalAwards=false
• 关键词: CAREER; SusChEM; New; Methods; Cu

In this (CAREER) project funded by the Chemical Catalysis Program of the Chemistry Division, Professor Michael K. Brown of the Department of Chemistry at Indiana University is introducing new methods for the catalytic construction of carbon-carbon bonds, which is an important objective in modern organic chemistry. The overarching goal of this research is to utilize inexpensive copper (Cu)-catalysts to assist in the synthesis of useful molecules such as new pharmaceutical agents. This new catalytic method promotes sustainability by using first row (non-precious metal) copper catalysts. Such catalyst are more abundant, less toxic and less environmentally harmful than precious metal catalysts. The educational goal is accomplished by developing engaging chemistry-themed classroom activities and by evaluating, improving and replicating a permanent chemistry-themed exhibit at a children's museum recently developed by the Brown Lab. These activities introduce and connect a known concept, smell, to something unknown, chemical structure. Professor Brown's efforts meet two needs in science education: development of chemistry-themed exhibits at science museums, and introduction of chemistry to children at a young age.Professor Brown is developing two general classes of Cu-catalyzed methods for carbon-carbon bond formation: 1) Suzuki-Miyaura-type cross-coupling reactions, and 2) Suzuki-Miyaura-type cross-coupling reactions that are interrupted by an alkene. Implementation of these methods enables chemists in academia and industry to access complex molecular scaffolds that were previously difficult to prepare. The impacts and intellectual merit of these studies are expected to be the following: 1) introduction of inexpensive, sustainable Cu-catalysts for Suzuki-Miyaura-type cross-couplings, 2) discovery of new methods for the functionalization of readily available unactivated alkenes, and 3) uncovering new modes of reactivity with Cu-catalysts. This research promotes sustainable chemistry by using first row (non-precious metal) copper catalysts. The educational goal is accomplished by developing fun and engaging organic chemistry-themed classroom activities and by evaluating, improving and replicating a permanent organic chemistry themed exhibit at a children's museum recently developed by the Brown Lab. These activities introduce and connect a known concept, smell, to something unknown, chemical structure. As the educational component of his project, Professor Brown is developing materials that educate children in grades K-6 about very basic concepts related to molecular structure and organic chemistry.

在这个由化学系化学催化项目资助的（CAREER）项目中，印第安纳大学化学系的Michael K. Brown教授正在介绍催化构建碳-碳键的新方法，这是一个重要目标现代有机化学。 这项研究的首要目标是利用廉价的铜（Cu）催化剂来协助合成有用的分子，例如新的药剂。 这种新的催化方法通过使用第一排（非贵金属）铜催化剂来促进可持续性。 这种催化剂比贵金属催化剂更丰富、毒性更小、对环境的危害更小。 该教育目标是通过开展引人入胜的化学主题课堂活动以及评估、改进和复制布朗实验室最近开发的儿童博物馆中的永久性化学主题展览来实现的。 这些活动引入已知的概念（气味）并将其与未知的化学结构联系起来。 布朗教授的努力满足了科学教育的两个需求：在科学博物馆开发化学主题展品，以及向儿童介绍化学。布朗教授正在开发两类通用的铜催化碳-碳键形成方法： 1) Suzuki-Miyaura型交叉偶联反应，和2)被烯烃中断的Suzuki-Miyaura型交叉偶联反应。 这些方法的实施使学术界和工业界的化学家能够获得以前难以制备的复杂分子支架。 这些研究的影响和智力价值预计如下：1）为铃木-宫浦型交叉偶联引入廉价、可持续的铜催化剂，2）发现易于获得的未活化烯烃功能化的新方法， 3）发现铜催化剂的新反应模式。这项研究通过使用第一排（非贵金属）铜催化剂来促进可持续化学。 该教育目标是通过开展有趣且引人入胜的有机化学主题课堂活动以及评估、改进和复制布朗实验室最近开发的儿童博物馆中的永久性有机化学主题展览来实现的。 这些活动引入已知的概念（气味）并将其与未知的化学结构联系起来。 作为其项目的教育组成部分，布朗教授正在开发材料，向 K-6 年级的儿童传授与分子结构和有机化学相关的非常基本的概念。

项目成果

Synthesis of Bisheteroarylalkanes by Heteroarylboration: Development and Application of a Pyridylidene–Copper Complex

杂芳基硼化合成双杂芳基烷烃：吡啶叉铜配合物的开发与应用

• DOI: 10.1002/anie.201902238
• 发表时间: 2019-03
• 期刊: Angewandte Chemie International Edition
• 作者: Huang, Yuan;Brown, M. Kevin
• 通讯作者: Brown, M. Kevin

Stereoselective [4+2]‐Cycloaddition with Chiral Alkenylboranes

立体选择性 [4 2] — 与手性烯基硼烷的环加成

• DOI: 10.1002/anie.202000652
• 发表时间: 2020-05
• 期刊: Angewandte Chemie International Edition
• 作者: Ni, Dongshun;Witherspoon, Brittany P.;Zhang, Hong;Zhou, Chen;Houk, K. N.;Brown, M. Kevin
• 通讯作者: Brown, M. Kevin