Table 1 Generation of acyl-substituted aryllithiums and reactions with electrophiles in a flow-microreactor system.

Entry	Electrophile	Yield*	Entry	Electrophile	Yield*
1	MeOH	90 (91^†)	13	PhNCO	87
2	Me₃SiOTf	86 (91^†)	14	MeOH	78^†
3	Bu₃SnCl	86	15	PhCHO	73 (75^†)
4	MeO₂CCl	68 (70^†)	16	PhCOMe	76
5	PhCOMe	81	17	PhNCO	71
6	PhCOCy	81	18	MeOH	67^†
7	PhCHO	60	19	PhNCO	51
8	MeOH	83^†	20	MeOH	54 (76^‡)
9	Me₃SiOTf	81 (84^†)	21	PhCHO	78^‡
10	MeO₂CCl	65 (69†)	22	MeOH	74
11	MeOH	77^†	23	PhCHO	77
12	MeOTf	42^†	24	PhNCO	59

THF, tetrahydrofuran.
Reaction conditions: acyliodobenzene (0.20 M in THF), MesLi (1.3 equivalent in THF/hexane, generated in situ), electrophile (2.0 equivalent in THF or Et₂O), residence time in R²=0.003 s.
*Isolated yields unless otherwise stated.
^†GC (gas chromatography) yields obtained using an internal standard.
^‡Residence time in R²=0.0015 s.

Quick links

Search