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. Author manuscript; available in PMC: 2011 Feb 5.
Published in final edited form as: Org Lett. 2010 Feb 5;12(3):588. doi: 10.1021/ol902784q

Table 3.

Three-Component Coupling of Linchpin 11 with Various Nucleophiles and CCR with Phenyl Iodide

graphic file with name nihms-167148-t0038.jpg
entry nucleophile product
1 graphic file with name nihms-167148-t0039.jpg graphic file with name nihms-167148-t0040.jpg
22a: (62%)b,c
22b: (45%)b,d 		graphic file with name nihms-167148-t0041.jpg
22h: (64%)a
2 graphic file with name nihms-167148-t0042.jpg graphic file with name nihms-167148-t0043.jpg
22c: (65%)b,c
22d: (50%)b,d 		graphic file with name nihms-167148-t0044.jpg
22i: (56%)a
3 graphic file with name nihms-167148-t0045.jpg graphic file with name nihms-167148-t0046.jpg
22e: (66%)b,c
22f: (51%)b,d 		graphic file with name nihms-167148-t0047.jpg
22j: (61%)a
4 graphic file with name nihms-167148-t0048.jpg graphic file with name nihms-167148-t0049.jpg
22g: (58%)a,c,e 		NR

Conditions:

a

1 N HCl, rt, 10 min.

b

TBAF, rt, 1 h.

c

R = Allyl, Allyl bromide, rt, 2 h.

d

R = Ph, 3 mol % Pd(PPh3)4, Phenyl iodide THF, rt, 6 h.

e

No cross-coupling product was obtained due to catalyst poisoning by dithiane.