Table 1 Optimization of the reaction conditionsaView full size image

From: Metal-free photoinduced C(sp3)–H/C(sp3)–H cross-coupling to access α‑tertiary amino acid derivatives

Entry

Variation from the standard conditions

Yield (%)b

1

None

70 (18:1)

2

H2 instead of H1

64 (11:1)

3

H3 instead of H1

55 (15:1)

4

H4 instead of H1

53 (15:1)

5

H5 and H6 instead of H1

Trace

6

MeCN instead of t-BuCN

49 (4:1)

7

t-BuCO2Me instead of t-BuCN

48 (10:1)

8

DMF instead of t-BuCN

Trace

9

PhCF3 instead of t-BuCN

Trace

10

w/o light

ND

11

w/o H1

ND

12

w/o light, 120  °C

ND

13

(NH4)2S2O8, TBHP, DTBP, BPO, 100  °C

Trace

  1. aReaction conditions: 1 (0.1 mmol), 2 (0.5 mmol) and H1 (0.2 mmol) in t-BuCN (1.0 mL), irradiation with a 10 W purple LED (395 nm) under N2 at room temperature for 12 h, Isolated yield (3/3′).
  2. bThe number given in parentheses is the ratio of 3/3′ detected by 1H NMR. ND no detected; w/o without; DMF N,N-Dimethylformamide, TBHP t-butyl hydrogen peroxide, DTBP di-tert-butyl peroxide, BPO benzoyl peroxide.
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