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. 2020 Dec 10;60(2):711–715. doi: 10.1002/anie.202012654

Table 1.

Reaction optimization.[a] Inline graphic

Entry

TEMPO

(equiv)

Solvent

T

Yield 1 a

[%]

1[b]

5

n ‐hexane

rt

59

2[c]

2

n‐hexane

rt

35

3[b]

10

n‐hexane

rt

57

4[b]

5

n‐hexane

0 °C

59

5[b]

5

PhMe

0 °C

60

6

5

MeCN

rt

58

7

5

MeCN

0 °C

50

8

5

MeCN

−20 °C

56

9

5

1,2‐DCE

rt

34

10[d]

5

MeCN

70 °C

30

11[e]

5

MeCN

rt

53

[a] Reaction conditions: 4 a (0.1 mmol, 1.0 equiv), TEMPO (0.5 mmol, 5.0 equiv), CsF (0.3 mmol, 3.0 equiv), and solvent (1 mL, 0.1 m). Yields represent isolated yields. [b] 18‐crown‐6 ether (0.3 mmol, 3.0 equiv) was added. [c] CsF (0.2 mmol, 2.0 equiv) and 18‐crown‐6 ether (0.2 mmol, 2.0 equiv) were used. [d] K2CO3 (0.40 mmol, 4.0 equiv) and 18‐crown‐6 ether (0.40 mmol, 4.0 equiv) were used to prepare the aryne. [e] Tetrabutylammonium difluorotriphenylsilicate (TBAT, 0.30 mmol, 3.0 equiv) was used to prepare the aryne. rt=room temperature.