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Design of a Versatile and Improved Precatalyst Scaffold for Palladium-Catalyzed Cross-Coupling: (η3-1-tBu-indenyl)2(μ-Cl)2Pd2

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Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, United States
Centre for Theoretical and Computational Chemistry (CTCC), Department of Chemistry, University of Oslo, P.O. Box 1033, Blindern, 0315 Oslo, Norway
§ Department of Process Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, United States
Cite this: ACS Catal. 2015, 5, 6, 3680–3688
Publication Date (Web):May 6, 2015
https://doi.org/10.1021/acscatal.5b00878
Copyright © 2015 American Chemical Society

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    Abstract

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    We describe the development of (η3-1-tBu-indenyl)2(μ-Cl)2Pd2, a versatile precatalyst scaffold for Pd-catalyzed cross-coupling. Our new system is more active than commercially available (η3-cinnamyl)2(μ-Cl)2Pd2 and is compatible with a range of NHC and phosphine ligands. Precatalysts of the type (η3-1-tBu-indenyl)Pd(Cl)(L) can either be isolated through the reaction of (η3-1-tBu-indenyl)2(μ-Cl)2Pd2 with the appropriate ligand or generated in situ, which offers advantages for ligand screening. We show that the (η3-1-tBu-indenyl)2(μ-Cl)2Pd2 scaffold generates highly active systems for a number of challenging cross-coupling reactions. The reason for the improved catalytic activity of systems generated from the (η3-1-tBu-indenyl)2(μ-Cl)2Pd2 scaffold compared to (η3-cinnamyl)2(μ-Cl)2Pd2 is that inactive PdI dimers are not formed during catalysis.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acscatal.5b00878.

    • Characterizing data; further experimental details; X-ray information for 2b-IPr, 2c-IPr, 2d-IPr, and 3; and details of DFT calculations (PDF)

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