Nickel boride mediated chemoselective deprotection of 1,1-diacetates to aldehydes and deprotection with concomitant reduction to alcohols at ambient temperature

ABSTRACT

A variety of 1,1-diacetates have been chemoselectively and efficiently deprotected to the corresponding aldehydes as well as deprotected and concomitantly reduced to the corresponding alcohols in high yields at ambient temperature with nickel boride generated in situ using different molar ratios of sodium borohydride and nickel (II) chloride in methanol at room temperature. Deprotection and reduction of a variety of aromatic, aliphatic and heterocyclic acylals have been achieved efficiently. Mild reaction conditions, easy work-up, high yields and chemoselectivity demonstrate the efficiency of this new method.

GRAPHICAL ABSTRACT

KEYWORDS:

• 1,1-Diacetates
• alcohol
• aldehyde
• deprotection
• nickel boride
• reduction

Acknowledgments

Gaurav Bartwal and Mohit Saroha thank CSIR, New Delhi, India for the grant of JRF and SPM fellowships, respectively.