Table 1 Investigation of oxidants and hydride acceptorsa.

From: Empowering alcohols as carbonyl surrogates for Grignard-type reactions

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Entry

Oxidant

Result

Entry

Oxidant

Result

1

None

9%

5

Isoprene

0

2b

Air

Trace

6

Ag2O

Trace

3c

O2

0

7

CuO

15%

4

NCS

0

8

DCB

21%

  1. aReaction conditions: 1a (0.25 mmol), 2a (0.2 mmol), Ru(PPh3)3Cl2 (3 mol %), dcypf (3 mol %), K3PO4 (1.1 equiv), oxidant (2.0 equiv), solvent (0.2 mL) at 70 °C under N2 atmosphere. See Supplementary Information (SI) for details. 1H NMR yield was determined using mesitylene as an internal standard. A ‘trace’ amount of product was noted when the desired product was not clearly detected.
  2. bThe reaction was performed under air.
  3. cOxygen balloon was used to provide O2 gas during the reaction.
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