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Bis(2-pyridyl)silane ligands. 2. Structural characterization and catalytic applications of palladium complexes in organostannane cross-coupling reactions

Journal Article · · Organometallics; (USA)
DOI:https://doi.org/10.1021/om00116a009· OSTI ID:7108068
 [1];  [2]
  1. Utah State Univ., Logan (USA)
  2. Naval Weapons Center, China Lake, CA (USA)
The synthesis and characterization of (R{sup 1}R{sup 2}Si(2-pyridyl))PdCl{sub 2} (R{sup 1} = Me, R{sup 2} = phenyl; 3) are presented. Complex 3 crystallizes in the monoclinic space groups P2{sub 1}/n (Z=4) with {beta} = 99.98 (1){degree} and a = 12.208 (2) {angstrom}, b = 12.651 (3) {angstrom}, c = 14.079 (2) {angstrom}. The single-crystal study showed the six-membered chelate ring to be in a boat conformation with the palladium and silicon atoms as the apexes out of plane. Cross-coupling reactions of organostannanes catalyzed by (Me{sub 2}Si(2-pyridyl))PdCl{sub 2} (2) were examined. Vinyltributylstannane undergoes cross coupling in high yield when treated with benzoyl chloride and 1 mol % of 2 in di- chloromethane, whereas treatment with iodobenzene results in formation of Me{sub 2}Si(2-pyridyl)PdI{sub 2} (4) with only a minor amount of cross coupling observed. The addition of LiCl did not affect the cross-coupling reaction when (PPh{sub 3}){sub 2}PdCl{sub 2} was used as the precatalyst. When trimethyl(phenylethynyl)stannane was used, the addition of lithium chloride did not decrease homocoupling of the organostannane reagent for precatalyst 2, whereas for (Ph{sub 3}P){sub 2}PdCl{sub 2} homocoupling of the stannane partner was not observed with or without added lithium chloride.
OSTI ID:
7108068
Journal Information:
Organometallics; (USA), Journal Name: Organometallics; (USA) Vol. 9:2; ISSN 0276-7333; ISSN ORGND
Country of Publication:
United States
Language:
English