Heterobiaryl synthesis by contractive C–C coupling via P(V) intermediates | Zendy

Michael C. Hilton | Zendy; Xuan Zhang | Zendy; Benjamin T. Boyle | Zendy; Juan V. AlegreRequena | Zendy; Robert S. Paton | Zendy; Andrew McNally | Zendy

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Heterobiaryl synthesis by contractive C–C coupling via P(V) intermediates

Author(s) -

Michael C. Hilton,

Xuan Zhang,

Benjamin T. Boyle,

Juan V. AlegreRequena,

Robert S. Paton,

Andrew McNally

Publication year - 2018

Publication title -

science

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 12.556

H-Index - 1186

eISSN - 1095-9203

pISSN - 0036-8075

DOI - 10.1126/science.aas8961

Subject(s) - diazine , chemistry , ligand (biochemistry) , coupling (piping) , pyridine , molecule , combinatorial chemistry , stereochemistry , regioselectivity , computational chemistry , medicinal chemistry , catalysis , organic chemistry , materials science , biochemistry , receptor , metallurgy

Heterocycles meet and marry on phosphorus Metals such as palladium are routinely used to link together carbon rings in pharmaceutical synthesis. However, the presence of nitrogen in both rings can trip up this process. Hiltonet al. report a versatile alternative process in which phosphorus takes the place of the metal. The phosphorus binds successively to both rings at the sites opposite the nitrogen, and treatment with acidic ethanol then pushes them off, bound to each other. Theory implicates a five-coordinate phosphorus intermediate that kinetically favors coupling of the two nitrogen-bearing rings over reactions of the other all-carbon substituents.Science , this issue p.799

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