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. Author manuscript; available in PMC: 2017 Aug 16.
Published in final edited form as: Acc Chem Res. 2016 Jul 29;49(8):1546–1556. doi: 10.1021/acs.accounts.6b00272

Table 1.

Reaction efficiency correlation with ‘BDFE’.

graphic file with name nihms827418u2.jpg
acid cat redox cat ‘BDFE’a % yieldb
none [Ru(bpy)3](BArF)2 -- 0
BzOH [Ru(bpy)3](BArF)2 45 0
Et3N•HBF4 [Ru(bpy)3](BArF)2 41 0
lutidine•HBF4 [Ru(bpy)3](BArF)2 35 0
(PhO)2PO2H [Ru(bpy)3](BArF)2 33 78
lutidine•HBF4 [Ir(ppy)2(dtbbpy)](PF6) 31 74
(PhO)2PO2H [Ir(ppy)2(dtbbpy)](PF6) 29 93
PTSA [Ru(bpy)3](BArF)2 27 92
(PhO)2PO2H Ir(ppy)3 24 74
a

Effective ‘BDFE’ values were calculated from the thermodynamic cycle illustrated in Figure 2a using pKa and potential data in MeCN.

b

Yields determined by GC analysis of crude reaction mixtures relative to internal standard. Isomeric ratios are ~5:1 in all cases, favoring the cis stereoisomer which spontaneously lactonizes to form product 4-cis.