Synthesis of Pyridiniumboranephosphonate Diesters and Related Compounds using Trityl Cation as a Borane Hydride Acceptor

Abstract

Boranephosphonate diesters react with pyridine and some tertiary amines in the presence of dimethoxytrityl chloride used as a borane­ hydride acceptor, to afford the boron-modified phosphodiester analogues containing a P-B-N structural motif. The reaction provides a convenient entry to pyridinium- and ammoniumboranephosphonates derived from the corresponding alkyl, aryl, or nucleoside boranephosphonate diesters. Some aspects of the synthetic protocol, mechanistic features related to a possible intermediate involved, and the role of the solvents used, are discussed.

Key words

H-phosphonates - boranephosphonates - pyridinium­boranephosphonates - trityl cation - nucleotide analogues

Publikationsverlauf

Eingereicht: 01. September 2020

Angenommen nach Revision: 06. Oktober 2020

Artikel online veröffentlicht:
09. November 2020

• References and Notes

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