Table 3.

Phenylation and oxidation of alcohol 3 b.^[a]

Entry	Base	Solvent	Additive (equiv)	4 c [%][b]	9 [%][b]
1	tBuONa	toluene	–	21	60
2	tBuONa	toluene	piperidine (1.2)	14	54
3	NaHMDS	pentane	–	9	35
4	NaHMDS	pentane	piperidine (1.2)	5	30
5[c]	NaH	TBME	–	30	53
6[c,d]	NaH	TBME	–	11	65
7	tBuONa	THF	–	10	31
8	tBuONa	THF	DPE (1.2)	21	39
9	tBuONa	THF	TEMPO (1.2)	24	43

[a] Reaction conditions: see the Supporting Information. [b] ¹H NMR yields using TMB as internal standard. [c] 3 b in excess, 50 °C for 1 h, isolated yields. [d] Ph(Mes)IBr was used instead of 1 d, chemoselectivity Ph:Mes 2:1.