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. Author manuscript; available in PMC: 2010 Apr 3.
Published in final edited form as: J Org Chem. 2009 Apr 3;74(7):2873–2876. doi: 10.1021/jo900163w

TABLE 3.

Strecker reactions of various ketones and amines in the presence of palladium complex 2.a

graphic file with name nihms100561t48.jpg

Entry Aldehyde Amine Product Conv.(Yield) (%)
1 graphic file with name nihms100561t49.jpg graphic file with name nihms100561t50.jpg graphic file with name nihms100561t51.jpg 99 (92)
2 graphic file with name nihms100561t52.jpg graphic file with name nihms100561t53.jpg graphic file with name nihms100561t54.jpg 86 (74)
3 graphic file with name nihms100561t55.jpg graphic file with name nihms100561t56.jpg graphic file with name nihms100561t57.jpg 95 (88)
4 graphic file with name nihms100561t58.jpg graphic file with name nihms100561t59.jpg graphic file with name nihms100561t60.jpg 17 (15)
5 graphic file with name nihms100561t61.jpg graphic file with name nihms100561t62.jpg graphic file with name nihms100561t63.jpg 44 (40)
6 graphic file with name nihms100561t64.jpg graphic file with name nihms100561t65.jpg graphic file with name nihms100561t66.jpg 85 (83)
7 graphic file with name nihms100561t67.jpg graphic file with name nihms100561t68.jpg graphic file with name nihms100561t69.jpg 49 (33)
8 graphic file with name nihms100561t70.jpg graphic file with name nihms100561t71.jpg graphic file with name nihms100561t72.jpg 58 (35)
9 graphic file with name nihms100561t73.jpg graphic file with name nihms100561t74.jpg graphic file with name nihms100561t75.jpg 62 (55)
10 graphic file with name nihms100561t76.jpg graphic file with name nihms100561t77.jpg graphic file with name nihms100561t78.jpg 68 (60)
a)

To a mixture of palladium catalyst, sodium sulfate (100mg, 0.7 mmol), 7 (0.2 mmol), and 8 (0.52 mmol) in 1 mL CH2Cl2 in Schlenk tube was added dropwise 9 (0.4 mmol). The mixture was stirred for 24 hrs at room temperature. If necessary, compounds were purified by column chromatography on silica gel with a gradient elution of hexanes/ethyl acetate.

b)

Isolated yields.