Mono-N-protected amino acid ligands stabilize dimeric palladium(II) complexes of importance to C–H functionalization

Gair, Joseph J.; Haines, Brandon E.; Filatov, Alexander S.; Musaev, Djamaladdin G.; Lewis, Jared C.

doi:10.1039/c7sc01674c

Title: Mono-N-protected amino acid ligands stabilize dimeric palladium(II) complexes of importance to C–H functionalization

Journal Article · Fri Jun 16 00:00:00 EDT 2017 · Chemical Science

DOI:https://doi.org/10.1039/c7sc01674c· OSTI ID:1390852

^[1];

^[2]; Filatov, Alexander S. ^[1];

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^[1]

Univ. of Chicago, IL (United States)
Emory Univ., Atlanta, GA (United States)

Mono-protected amino acid (MPAA) ligands are used in a number of Pd-catalyzed C–H functionalization reactions. MPAAs have been proposed to bind to Pd(II) via κ²-(N,O) coordination, but such binding has not yet been experimentally validated. Herein, we report the synthesis and detailed characterization of a series of MPAA complexes prepared via cyclopalladation of dimethylbenzylamine in the presence of MPAAs. The isolated complexes exist as μ-carboxylato (MPAA) bridged dimers and feature potential M–M cooperativity and secondary sphere hydrogen bonding. Selective MPAA coordination and relay of stereochemistry, previously suggested to uniquely result from κ²-(N,O) MPAA coordination, are both observed. The isolated MPAA complexes undergo C–C and C–X (X = Cl, Br, I) bond formation when treated with electrophiles used for catalytic C–H functionalization. Stoichiometric iodination of MPAA palladacycles was found to proceed via a dinuclear palladium species with one equivalent of iodine in the rate limiting transition structure, and the isolated complexes also served as viable precatalysts for catalytic C–H functionalization. Together, these results provide a number of insights into the reactivity of Pd-MPAA complexes relevant to C–H bond functionalization.

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Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Science (SC)

Grant/Contract Number:: CHE-0958205; AC02-06CH11357; NSF/CHE-1346572

OSTI ID:: 1390852

Journal Information:: Chemical Science, Vol. 8, Issue 8; ISSN 2041-6520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: ENGLISH

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Cited by: 32 works

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