posted on 2021-03-30, 17:04authored byNa Meng, Wensheng Yu, Takao Suzuki, Maofen Chen, Zhiqi Qi, Bin Hu, Jianming Bao, John S. Debenham, Robert Mazzola, Joseph L. Duffy
A mild
condition via PPh3/I2/imidazole for
the deoxygenation of substituted methanol derivatives has been identified.
This metal-free process was found to proceed well on secondary or
tertiary alcohols substituted with one or two heteroaryl groups, and
it tolerates acid-sensitive heterocycles. This condition works for
methanol derivatives substituted with 2-pyridyl, 4-pyridyl, or other
heterocyclic groups, allowing the negative charge formed during the
reaction to resonate to a nitrogen atom. Methanol derivatives substituted
with 3-pyridyl or heterocyclic groups that do not allow the negative
charge formed during the reaction to resonate to a nitrogen atom will
not undergo deoxygenation under this condition.