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. Author manuscript; available in PMC: 2008 Aug 22.
Published in final edited form as: Org Lett. 2007 Jan 18;9(2):363–366. doi: 10.1021/ol062885a

Table 4.

Pd(OAc)2-Catalyzed Domino Carbopalladation-Cross-coupling of Internal Alkynes and Hindered Grignard Reagents a

graphic file with name nihms61791f5.jpg
entry graphic file with name nihms61791t50.jpg graphic file with name nihms61791t51.jpg graphic file with name nihms61791t52.jpg yield(%)b
1 graphic file with name nihms61791t53.jpg graphic file with name nihms61791t54.jpg graphic file with name nihms61791t55.jpg 71
2 graphic file with name nihms61791t56.jpg graphic file with name nihms61791t57.jpg graphic file with name nihms61791t58.jpg 65
3 graphic file with name nihms61791t59.jpg graphic file with name nihms61791t60.jpg graphic file with name nihms61791t61.jpg 72
4 graphic file with name nihms61791t62.jpg graphic file with name nihms61791t63.jpg graphic file with name nihms61791t64.jpg 69
5 graphic file with name nihms61791t65.jpg graphic file with name nihms61791t66.jpg graphic file with name nihms61791t67.jpg 60
6 graphic file with name nihms61791t68.jpg graphic file with name nihms61791t69.jpg graphic file with name nihms61791t70.jpg 81
7 graphic file with name nihms61791t71.jpg graphic file with name nihms61791t72.jpg graphic file with name nihms61791t73.jpg 78
8 graphic file with name nihms61791t74.jpg graphic file with name nihms61791t75.jpg graphic file with name nihms61791t76.jpg 74
9 graphic file with name nihms61791t77.jpg graphic file with name nihms61791t78.jpg graphic file with name nihms61791t79.jpg 81
a

Reaction conditions: alkyne (1.0 equiv), Grignard reagent (4.0 equiv), 1,2-dibromoethane (1.5 equiv), Pd(OAc)2 (5%), PPh3 (20%), THF (2 mL), refluxing, 30–40 h.

b

Isolated yields.