Enabling reactions

My PhD student Jeff St. Denis gave a great Monday Night Seminar tonight. He talked about his efforts to develop practical boron transfer reagents. “Enabling” is one of the keywords we emphasize in our research as we try to look at synthetic methods through the prism of enablement. In brief, it’s all about going after reactions or reagents that make people want to use them because there are no good alternatives. Together with Ved Srivastava, we even resorted to the “enabling” angle as a motto for the 2015 American Peptide Symposium we are putting together (www.aps2015.org).

Now… This might sound like a blasphemy given my stated position on the matter, but it is important to keep in mind that enabling and practical organic transformations, while significant, are not the only game in town when it comes to modern synthetic chemistry. To a large extent, the tough funding situation is behind the push for practical reactions and research motivated by somewhat political motives. However, time and again I am reminded about some really accomplished people who have reached great heights with roots in very basic, fundamental chemistry. And these people are not necessarily in academia.

Take my friend Robert Gnann. Robert hails from Germany, where he did his doctoral training. I met Robert in Los Angeles some 20 years ago and we had a great time there while he was a postdoc with Carl Christie. Throughout the years I have marveled at some of the things Robert had done during his PhD. Take a look at some of the chemistry developed by him and his PhD advisor, Professor Naumann. In this sequence, you take xenon difluoride and exchange its fluoride ligands for a trifluoroacetate and a triflate. When the resulting molecule is exposed to an aromatic compound, electrophilic substitution ensues. What is this? A “xenonoation” of sorts, I suppose… I am showing the Xe-triflate bond in covalent terms, but it is, of course, ionic. I love inert gas transformations and, while this chemistry has no immediate applications, it is intellectually stimulating and exceptionally challenging due to the sheer instability of everything involved in it. In my view, “enabling” is not to be equated with immediate and obvious field of use. It is sad that the dogmas of green chemistry (seriously – recall those 10 commandments, it is almost Marxist the way people show them in talks) have been influencing our thinking a bit too much and “blue sky” research is no longer en vogue.

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http://onlinelibrary.wiley.com/doi/10.1002/zaac.19976231127/abstract

By the way, Robert is a big cheese now, he is Momentive’s senior vice president and managing director of silicones in Europe, the Middle East, Africa and India. He has not been doing research for a long time, but the foundation of his training lies in exploring some fascinating inert gas chemistry in the Naumann lab. The inorganic synthesis training he received came with a good dose of attention to “minesweeping techniques” aimed at matter that is shock-sensitive even at -50 C. I bet this training teaches attention to detail because, if there is one wrong step, the game’s over… I am willing to bet that this background has helped Robert navigate the rough waters of global business.

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