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DOI: 10.1055/sos-SD-025-00443

Schall, A.; Reiser, O.Science of Synthesis, (200725636.

Chloroiminium salts 36, generated by addition of gaseous hydrogen chloride to anhydrous hydrogen cyanide in the presence of aluminum trichloride or zinc(II) chloride, are highly reactive formylating reagents (Scheme 20). This process, known as the Gatterman reaction, is especially useful for the formylation of phenols and hetarenes (Table 17);[‌4‌] however, in contrast to the VilsmeierHaack reaction, discussed in Section, aromatic amines are not compatible substrates. In return, already weakly activated benzenes such as xylenes can be formylated in good yields (Table 16). The isolation of the resulting aldehydes in pure form is especially facile, because the aldiminium salt 37 often precipitates from the reaction mixture and can then be isolated by simple filtration and subsequently hydrolyzed to give the aromatic aldehyde.

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Meeee Me8 Meeeeeee Meeee (%) Mee
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8 8,8-Me8M8M8 MMe, MMM, MeMe8 88 [‌888‌]
8 8-MMM8M8 MMe, MMM, MeMe8 88 [‌888‌,‌888‌]
8 8-MeMM8M8 MMe, Me(MM)8, MeMe8 88 [‌888‌,‌888‌]
8 MMe, Me(MM)8, MeMe8 88 [‌888‌]
8 MMe, Me(MM)8 88 [‌888‌]
8 MMe, Me(MM)8, MeMe8 88 [‌888‌]
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8 MMe, MMM, Me(MM)8 88 [‌888‌]
88 MMe, Me(MM)8, MeMe8 88 [‌88‌]
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Meeee Meeeeeeee Meeeeeee Meeee (%) Mee
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8 MMe, MMM, MeMe8 88 [‌888‌,‌888‌]
8 MMe, MMM, MeMe8 88 [‌888‌]
8 MMe, MMM, MMMe8 88 [‌888‌]
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