Table 2. Evaluation of Functional Groups on the Catalytic Performance.

entry	R1	R2	R3	conversion (%)a
1	Me	Ac	H	92 (62)b
2c	Me	Ac	H	73
3d	Me	Ac	H	72
4	Me	Ac	Me	60
5	Me	Ac	OMe	83
6	Me	Ac	F	76
7	Me	Ac	OH	82
8	Me	Ac	CH2OH	98
9	Me	Ac	NMe2	82
10	Me	H (−NH3+)	H	<1
11	Me	NAc-Gly-	H	50
12	H (−COOH)	Ac	H	53
13	–Ala-OMe	Ac	F	73
14	NAcTrpLysLeuValGlyAlaOH		F	74 (95)e

^aConversion of the tryptophan reactant with 2 mol % Pd and atmospheric oxygen pressure, as determined via HPLC using a calibration curve. The major product peak was identified as the arylated product via LC-MS (see the Supporting Information).

^bReaction performed on a 1 mmol scale (0.0375 M) in an open flask.

^cReaction with phenylboronic acid pinacol ester (1.5 equiv).

^dReaction with potassium phenyltrifluoroborate (1.5 equiv).

^eReaction performed with 6 mol % Pd(OAc)₂/4,5-diazafluoren-9-one.