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3.16.4.2 α-Perfluoroalkylation Reactions

DOI: 10.1055/sos-SD-203-00422

MacMillan, D. W. C.; Watson, A. J. B.Science of Synthesis: Stereoselective Synthesis, (20113739.

The photoredox aldehyde alkylation procedure (described in Section 3.16.4.1) has been extended to encompass α-perfluoroalkylation.[‌31‌] This transformation is mechanistically and operationally similar to the original procedure and requires the same organocatalyst 86 (albeit a different acid salt). The mild reaction conditions enable facile access to functionalized fluorinated compounds (e.g., 89) of particular synthetic value in a number of important research areas (Scheme 28).[‌124‌‌129‌] Importantly, the scope of the reaction is not limited to conventionally favored trifluoromethylation and can be readily applied to higher homologues.

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M8 M8 ee (%) Meeee (%) Mee
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(M)-MM(Me)Me M 88e 88 [‌88‌]
(MM8)8Me (MM8)8MM8 88 88 [‌88‌]
(MM8)8Me M8M8 88 88 [‌88‌]
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References


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