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. Author manuscript; available in PMC: 2016 Mar 11.
Published in final edited form as: J Am Chem Soc. 2015 Mar 3;137(9):3338–3351. doi: 10.1021/ja512690x

Table 6.

Additive Screening in the Arylation of Phenylalaninea,b

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Entry Additives (equiv) % Yield
1 no 10
2 K2CO3 0
3 KHCO3 8
4 K3PO4(0.5) 14
5 K2HPO4 40
6 KH2PO4 30
7 KF 16
8 Na2HPO4 32
9 NaH2PO4•H2O 50
10 NaH2PO4 49
11 LiH2PO4 36
12 LiOAc 0
13 NaH2PO4•H2O(1.5) 56
14 NaH2PO4•H2O (2) 66
15 NaH2PO4•H2O (3) 72
16 NaH2PO4•H2O (4) 70
a

Conditions: Substrate 2′ (0.1 mmol), Pd(OAc)2 (10 mol%), AgOAc (0.2 mmol), p-Tol–I (0.3 mmol), L1 (20 mol%), HFIP (1.0 mL), 100 °C, 36 h.

b

Determined by 1H NMR analysis of the crude product using CH2Br2 as an internal standard.