Monday, September 12, 2011

BrettPhos, an organic compound and ligand named after Brett Fors of MIT's Buchwald Lab

BrettPhos is named after Brett Fors of  Stephen L. Buchwald's lab at MIT [1]. Spelling and pronunciation of this chemical compound name resembles the spelling and pronunciation of the name of its designer. The word part Phos, substituting for Fors, hints at the phosphorus atom in the molecular structure of  BrettPhos and its formal derivation from phosphane (phosphine). Systematic names for BrettPhos are 2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl and dicyclohexyl-[3,6-dimethoxy-2-(2,4,6-triisopropylphenyl)phenyl]phosphane. The molecular formula is C35H53O2P.

BrettPhos is a promising and effective ligand in metal-catalyzed synthesis including palladium-catalyzed cross-coupling reactions, Suzuki coupling, trifluormethylation reactions and fluorinations [1-3].

A SMILES notation for BrettPhos:  

[1] Profiles from NOS: Brett Fors: The Guy With The Namesake Ligand. Chemical & Engineering News July 11, 2011, 89 (28), page 34 []. 
[2] B. P. Fors, D. A. Watson, M. R. Biscoe and S. L. Buchwald: A Highly Active Catalyst for Pd-Catalyzed Amination Reactions: Cross-Coupling Reactions Using Aryl Mesylates and the Highly Selective Monoarylation of Primary Amines Using Aryl Chlorides. J. Am. Chem. Soc. October 2008, 130 (41), 13552-13554 [].
[3] Patent application by S. L. Buchwald, D. A. Watson, M. Su and G. Teverovskiy: Metal-catalyzed Carbon-Fluorine Bond Formation [].

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