The 2022 Organic Syntheses Lecturer is Guangbin Dong, Professor of Chemistry at the University of Chicago. The seminar is entitled, "Merging C−C and C−H Activation: Palladium/Norbornene Cooperative Catalysis." Hosted by Dirk Trauner.
In-person in Silver Center, room 101A (Jurow Lecture Hall) and on zoom.
Zoom Link: https://nyu.zoom.us/j/95144438814?pwd=YS9vNHZDLzlEMUpIMkhod3dMYjVYUT09
For more information about Guangbin Dong, click here.
Abstract: Achieving site-selectivity in arene functionalization that is complementary to the one from electrophilic aromatic substitution (EAS) reactions has been a long-standing quest in organic synthesis. The palladium/norbornene (Pd/NBE) cooperative catalysis potentially offers a unique approach to this problem, but its usage has been hampered by “three constraints”: the electrophile constraint, the arene-substrate constraint, which is the requirement of using aryl iodides, and the “ortho constraint”, which is the requirement of an ortho substituent for mono ortho functionalization of haloarenes. Here, we show that all these three constraints could be addressed through designing the electrophiles, phosphine ligands and norbornene ligands. Besides Catellani-type ortho alkylation and arylation, new ortho functionalization methods, such as ortho amination, acylation, carboxylation, thiolation and annulation, have been realized. In addition, using a unique phosphine system, various aryl bromides can be employed as the arene substrates. Moreover, a new class of bridgehead-modified NBEs overcomes the “ortho” constraint, thereby enabling a broadly useful strategy for arene functionalization with complementary site-selectivity to EAS reactions. A range of ortho-unsubstituted aryl iodides, previously problematic substrates, now can be employed to provide mono ortho functionalized products effectively. These methods are applicable for late-stage functionalization of complex bioactive molecules at positions that are difficult to be reached by conventional approaches
The Organic Syntheses Lectureship
Since 1921, Organic Syntheses has provided the chemistry community with collections of detailed, reliable, and carefully checked procedures for the synthesis of organic compounds. Some procedures describe practical methods for the preparation of specific compounds of interest, while other procedures illustrate important synthetic methods with general utility. Each procedure is written in considerably more detail than typical experimental procedures in journals and each reaction and all characterization data will have been carefully "checked" for reproducibility in the laboratory by a member of the Board of Editors. Roger Adams and the organization’s other founding fathers created “the lasting legacy of Organic Syntheses as the ‘gold standard’ of experimentation in organic chemistry”. Directions for submitting or recommending procedures for checking and publication are found at orgsyn.org. Organic Syntheses, Inc., is operated with book and database royalties from John Wiley and Sons and investment income. Also key to the operation are donations of services, chemicals, etc. by individuals and institutions in the course of checking procedures. In addition to partially underwriting the cost of testing and preparing procedures for publication, the organization • maintains a free fully searchable data-base website (orgsyn.org) of all its tested procedures • provides lectureship grants to universities, summer research grants to undergraduate institutions, assists select Gordon Research Conferences and the ACS Org. Division Graduate Research Symposium and sponsors a workshop for young investigators in synthetic organic chemistry. • co-sponsors with Organic Reactions Inc. the biannual ACS Roger Adams Award in Organic Chemistry. This lectureship series is made possible by a grant from Organic Syntheses, Inc.
