The Guy With The Namesake Ligand: Brett ForsTo troll the nightly poster sessions at the National Organic Symposium is to combine stargazing with a high school reunion. Nobel laureates rub elbows with undergraduates presenting their work. Graduate school labmates who haven’t seen each other in years catch up. And a spread of food, wine, and beer fuels attendees through the midnight hour.
It was here that I ran into Brett P. Fors, who just obtained his Ph.D. from Stephen Buchwald’s lab at MIT. Fors has already been accorded a privilege that few chemists can claim– he has a ligand named after him. I’ve had a longstanding interest in how chemists name things, so I couldn’t resist asking Fors about that ligand– better known as BrettPhos.
BrettPhos was designed to facilitate palladium-catalyzed cross-coupling reactions which form C-N bonds, in cases where the nitrogen comes from a primary amine. One challenge there was getting selective monoarylation- getting one aryl ring attached to the primary amine instead of two. BrettPhos pulls off monoarylation very well. But since the original report of BrettPhos, the Buchwald team has learned that the ligand is also effective in Suzuki coupling chemistry, trifluoromethylation reactions, and fluorinations.
“It’s opened up a lot of different doors, but it wasn’t the plan at first,” Fors says. “There was a lot of luck involved there.”
Fors says the ligand came into being during the middle of his first year in grad school. In addition to his coauthors on BrettPhos papers he had guidance from postdoctoral researcher David S. Surry, who today works as a technical advisor at New York law firm Ropes and Gray.
New ligands get named at the Buchwald group meeting, Fors explains. Originally, the ligand was going to be named BPhos, but another molecule had already claimed that name. So the privilege fell to Fors. He’s not the only member of the group to have a ligand named for him, and as The Sceptical Chymist has reported, some of Buchwald’s cats also have ligands named for them.
But Fors doesn’t call his ligand by its well-known name. “I actually can’t say it- it’s kind of weird,” he says. Hearing that reminded me of the informal etiquette I’ve picked up about named reactions in organic chemistry– that inventors of named reactions rarely use the proper names in their talks and papers, and are just about never the ones that coin those proper names in the first place.
Fors helped develop another ligand during his time in the Buchwald group. That ligand will be published soon and will be named after another Buchwald feline, he says. Next up for Fors is a postdoctoral stint at the University of California, Santa Barbara, with Craig Hawker. But Fors has something else on his agenda– to develop a ligand to name after his wife, Carly. (I think CarlyPhos has a nice ring to it.)