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. Author manuscript; available in PMC: 2014 Oct 9.
Published in final edited form as: J Am Chem Soc. 2013 Sep 27;135(40):14936–14939. doi: 10.1021/ja407822b

Table 2.

Effect of pH and Organic Co-solvent on Diazo Compound Formation by Phosphinoester 1

graphic file with name nihms528176t2.jpg
Entry Solventa Yield (%)b Entry Solventc Yield (%)b
1 pH 5.0 69 5 50% v/v MeOH 80
2 pH 6.0 88 6 50% v/v CH3CN 74
3 pH 7.0 91 7 50% v/v DMF 75
4 pH 8.0 71 8 1% v/v DMSO 74
9 20% v/v E.G. 78
a

10 mM sodium phosphate buffer.

b

Isolated yield.

c

In 10 mM sodum phosphate buffer, pH 7.0. E.G. = ethylene glycol.