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. Author manuscript; available in PMC: 2012 Apr 1.
Published in final edited form as: Org Lett. 2011 Mar 10;13(7):1852–1855. doi: 10.1021/ol2003572

Table 2.

Scope of Coupling with Diverse Heteroaryls

graphic file with name nihms280321u3.jpg
entry heteroaryl yield (%)a
1 graphic file with name nihms280321t1.jpg 2aa, 2ab C2:C4 (70:30) 44 (58)
2 graphic file with name nihms280321t2.jpg 2b R= Me
2c R= Cl		 65 (83)
56 (81)
3 graphic file with name nihms280321t3.jpg 2da
2db 		54% +
17% (92)
4 graphic file with name nihms280321t4.jpg 2e R= 3-CO2Me
2f R= 4-Br
2g R= 5-Br		 59 (75)
61 (80)
64 (82)
5 graphic file with name nihms280321t5.jpg 2h 59 (72)
6 graphic file with name nihms280321t6.jpg 2i 59 (81)b
7 graphic file with name nihms280321t7.jpg 2j 61 (70)
8 graphic file with name nihms280321t8.jpg 2k 34 (77)
9 graphic file with name nihms280321t9.jpg 2l R: H
2m R: Me		 60 (63)
60 (70)
10 graphic file with name nihms280321t10.jpg 2n 54 (76)
11 graphic file with name nihms280321t11.jpg 2o R= H
2p R= Br
2q R= Ph		 31 (93)
42 (54)
34 (66)
12 graphic file with name nihms280321t12.jpg 2r 11 (74)

Heterocycle (1.0 mmol), potassium cyclobutyltrifluoroborate (1.0 mmol), Mn(OAc)3 (2.5 mmol), TFA (1.0 mmol), AcOH/H2O 1:1 (0.08 M), 50 °C, 18 h.

a

Isolated yields and conversions (indicated in parentheses) determined by 1H NMR spectroscopic analysis of the crude mixture.

b

Heterocycle (1.0 mmol), potassium cyclobutyltrifluoroborate (3.5 mmol), Mn(OAc)3 (5.0 mmol), TFA (1.0 mmol), AcOH/H2O 1:1 (0.08 M), 50 °C, 18 h.