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Selectively perform cross-coupling reactions with this catalyst

By Tetsuo Satoh |

Twofold C–H activation and cross-coupling of stoichiometric amounts of organic molecules, R1–H and R2–H, to form an R1–R2 product that is free of homocoupling products (R1–R1 or R2–R2) is a goal to simplify organic synthesis of certain compounds. Up to now, the only reliable strategy to eliminate the homocoupling side products effectively is to use an excess of one reactant over another.

Now, professor Eiichi Nakamura and colleagues at the University of Tokyo (www.u-tokyo.ac.jp) have succeeded in performing a one-step conversion of stable C–H bonds into C–C bonds at mild conditions with 100% selectivity. For the first time, the researchers have discovered a simple and highly efficient way to produce certain kinds of organic compounds. The reported new method — which uses a novel iron catalyst — can not only simplify organic synthesis, but would greatly reduce costs and cut down on waste products, which could have huge implications for industrial production of pharmaceuticals, petrochemicals and more.

The method uses an N-(quinolin-8-yl)amide anion for a temporary connection, followed by the cross-coupling of a stoichiometric mixture of aromatic compounds. The reaction takes place under mildly oxidative, iron-catalyzed conditions, through the formation of a heteroleptic R1–M–R2 intermediate, and has a high yield without any trace of homocoupling products.

“I felt drawn to investigate the use of iron as a catalyst to speed up reactions,” says Nakamura. “It’s intriguing how on one hand it’s cheap, abundant and nontoxic, but on the other hand it’s difficult to control iron’s catalytic ability due to its complex electronic behavior.” Nakamura and colleagues were able to fine-tune a first-of-its-kind iron catalyst so that it selects which C–H bonds to combine and which bond pairings to reject.

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