Table 3.

C=H hetero-difunctionalization of BQ.

Entry	R	R′	Yield5[%][a]	Yield4[%][a]
1	p-MeO-C6H4	p-HO-C6H4	73 (5 j)	<5 (4 j)
2	m,p-(MeO)2-C6H3	p-HO-C6H4	71 (5 k)	10 (4 k)
3	m,p-(MeO)2-C6H3	p-MeO-C6H4	65 (5 l)	21 (4 l)
4	p-HO-C6H4	o-MeO-C6H4	50 (5 m)	41 (4 m)
5	m,p-(MeO)2-C6H3	p-EtO2C-C6H4	44 (5 n)	26 (4 n)
6	p-EtO2C-C6H4	m,p-(MeO)2-C6H3	48 (5 n)	16 (4 n)
7[d]	p-EtO2C-C6H4	p-F3C-C6H4	<5 (5 o)	47 (4 o)
8[b]	N-Boc-pyrrole-2	3-thiophene	trace	74 (4 p)
9[b–d]	m-O2N-C6H4	3-thiophene	trace	42 (4 q)
10[d]	p-EtO2C-C6H4	3-thiophene	trace	34 (4 r)
11	m,p-(MeO)2-C6H3	cyclohexyl	–[e]	–

^[a] Yields of isolated products.

^[b] 2.5 equiv of boronic acid 6 used.

[c] Treated with FeCl₃ at the end of reaction.

^[d] Product only moderately stable.

^[e] Complex mixture of products.