Table 1 Optimization and control studies.

From: Selective deoxygenative alkylation of alcohols via photocatalytic domino radical fragmentations

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Entry

Variation from optimized conditions

Yield (%)a

1

None

92 (89)b

2

P(OEt)3 instead of PPh3

84

3

[Ir(dFCF3ppy)2dtbbpy)](PF6) (1 mol %)

83

4

Na2CO3 instead of NaOtBu

0

5

No CS2

0

6

No PPh3

0

7

No photocatalyst

0

8

No light

0

9

Without H2O

26

10

3a (1.0 equiv)

66

11

PPh3 (0.20 equiv)

20

12

PPh3 (0.20 equiv) + reductants (2.0 equiv)

<20

  1. Standard procedure: 1aa (0.20 mmol), NaOtBu (1.0 equiv), THF (1.2 mL), CS2 (1.5 equiv), 3 h. After removing solvent in vacuo, then 3a (2.0 equiv), [Ir(ppy)2dtbbpy](PF6) (1 mol%), PPh3 (1.2 equiv), H2O (7.0 equiv), MeCN (2.0 mL), 24 h blue LED irradiation.
  2. Boc t-butoxycarbonyl.
  3. aDetermined by 1H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard.
  4. bIsolated yield.
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