Palladium-Catalyzed Transient Directing Group-Enabled Functionalization of Aliphatic Amines and Aldehydes

化学系的化学合成项目支持印第安纳州普渡大学化学与化学生物学系的葛海波教授的项目。胺是由氨通过有机基团取代一个或多个氢原子而衍生的有机化合物。 胺在生物学中非常常见，例如在氨基酸和神经递质中，包括肾上腺素、去甲肾上腺素、多巴胺、血清素和组胺。 这项研究的目的是将简单的胺转化为其他更有价值或有用的胺。为了解决这一挑战，葛教授和他的学生们正在使用“定向基团”，这些基团可逆地附着在胺基上，并迫使反应发生在特定的（所需的）位点上。夏季本科生研究计划吸引大学生，特别是女性和代表性不足的少数民族，到STEM领域，培养潜在的未来领导者在科学研究。 高中教师的参与提供了一个积极的学习环境，使他们能够深入了解关键的科学思想和实践，以他们的班级。化学系化学合成项目支持了印第安纳州普渡大学印第安纳波利斯分校（IUPUI）化学与化学生物学系葛海波教授的项目。葛教授正在开发构建碳-碳和碳-杂原子键的新方法。这种反应化学允许通过C-H键官能化过程以有效的方式容易地获得各种常见的有机化合物。 它还可以实现复杂有机分子的快速后期功能化（LSF）。与传统的交叉偶联反应相比，C-H官能化过程不需要预官能化的起始材料，并且可以避免使用化学计量的有机金属试剂，使其在环境和经济上更加有益。新型的C-H官能化反应允许使用容易获得的有机分子作为起始材料，从而提高了该方法的潜在应用。该项目的主要目标是开发新型过渡金属催化的C-H官能化反应，以提供强大，有价值和直接的合成方法来获得常见的有机框架。通过这种策略，预期从容易获得的脂肪族胺和醛中有效地获得各种医学上重要的（杂）环骨架。这些强sp3 C-H键的不对称官能化也设计了使用手性催化剂。该项目主要集中在合成有机和有机金属化学与计算和药物化学的潜在整合。因此，该项目非常适合教育和培训各级科学家。此外，一项针对高中教师的推广计划旨在使他们能够向课堂传授深入的关键科学思想和实践知识。该奖项反映了NSF的法定使命，并通过使用基金会的智力价值和更广泛的影响审查标准进行评估，被认为值得支持。

The Chemical Synthesis Program of the Chemistry Division supports the project by Professor Haibo Ge of the Department of Chemistry and Chemical Biology at Indiana University-Purdue University. Amines are organic compounds derived from ammonia by replacement of one or more hydrogen atoms by organic groups. Amines are very common in biology such as in amino acids and neurotransmitters including epinephrine, norepinephrine, dopamine, serotonin, and histamine. The goal of this research is to convert simple amines into other, more valuable or useful amines. To solve this challenge, Professor Ge and his students are using "directing groups" that attach reversibly to the amine group and force the reaction to occur on a specific (desired) site. The summer undergraduate research program attracts college students, especially women and underrepresented minorities, to the STEM areas, training potential future leaders in scientific research. The engagement of high school teachers provides an active learning environment and enables them to deliver in-depth knowledge of key scientific ideas and practices to their classes. This educational effort, in turn, triggers high school students' curiosity, inspires their interest in chemistry, and attracts more high school students into the STEM areas.The Chemical Synthesis Program of the Chemistry Division supports the project by Professor Haibo Ge of the Department of Chemistry and Chemical Biology at Indiana University-Purdue University Indianapolis (IUPUI). Professor Ge is developing new methods to construct carbon-carbon and carbon-heteroatom bonds. This reaction chemistry allows for various common organic compounds to be readily accessed in an efficient manner via a C-H bond functionalization process. It also enables rapid late-stage functionalization (LSF) of complex organic molecules. When compared to conventional cross-coupling reactions, the C-H functionalization process does not require pre-functionalized starting materials and can avoid the use of stoichiometric organometallic reagents, making it more environmentally and economically beneficial. The new type of C-H functionalization reactions allows for the use of readily-available organic molecules as starting materials, and thus improves the potential applications of the process. The principal goal of the project is to develop novel transition metal-catalyzed C-H functionalization reactions in order to provide powerful, valuable, and straightforward synthetic approaches to access common organic frameworks. A variety of medically important (hetero)cyclic skeletons are expected to be efficiently accessed from readily-available aliphatic amines and aldehydes via this strategy. The asymmetric functionalization of these strong sp3 C-H bonds is also designed with the use of chiral catalysts. The project focuses primarily on synthetic organic and organometallic chemistry with potential integration of computational and medicinal chemistry. Thus, the project is well-positioned for the education and training of all levels of scientists. Additionally, an outreach program with high school teachers is designed to enable them to deliver in-depth knowledge of key scientific ideas and practices to their classes.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.