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1.3.2.5 Borane-Catalyzed Reduction of Polycyclic Arenes

DOI: 10.1055/sos-SD-226-00066

Dai, X.; Shi, F.Science of Synthesis: Catalytic Reduction in Organic Synthesis, (20171143.

Tetrapropyldiborane can be used to catalyze the regioselective and partial reduction of naphthalene and its derivatives 22 at 200 °C under hydrogen pressures of 100 bar. Good to excellent yields of tetrahydroarenes 23 can be obtained by optimizing the amount of the catalyst. Hydrogenation of the naphthalene derivatives mainly occurs at the least substituted ring (Scheme 8).[‌40‌]

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Meeeeeeeeee 8

M8 M8 M8 M8 M8 M8 Meeeeeeee (eeee) Meeeeeee (eeee) Meeeee (%) Mee
M M M M M M 88 88 88 [‌88‌]
M M Me M M M 88 88 88 [‌88‌]
M M Me M M M 88 8 88 [‌88‌]
M M M Me M M 88 88 88 [‌88‌]
M M Me M M M 88 88 88 [‌88‌]
M M Me M M M 88 8 88 [‌88‌]
M M M Me M M 88 88 88 [‌88‌]
M M Me M Me M 88 88 88 [‌88‌]
M M Me M M Me 88 8 88 [‌88‌]
M M M Me Me M 88 88 88 [‌88‌]
Me M M Me M M 88 88 88 [‌88‌]
Me M M Me M M 88 8 88 [‌88‌]
M MM8MM8 M M M 88 88 88 [‌88‌]
M MM=MM M M M 88 88 8e [‌88‌]
M M Me M M M 88 8 88 [‌88‌]
M M M Me M M 88 8 88 [‌88‌]
M M M M 8-eeeeeeee M 8 8 88e [‌88‌]
M M MMe M M M 88 88 88 [‌88‌]
M M M MMe M M 88 88 88 [‌88‌]
M M MMMe8 M M M 88 88 88e [‌88‌]
M M Me M M M 88 88 88 [‌88‌]
M M M Me M M 88 8 88 [‌88‌]

e Meeeeeeeee ee MM.

e Mee eeeeeee ee 8,8,8e,8,8,8-eeeeeeeeeeeeeeeeeeeeeee (88, M8 = M8 = M8 = M8 = M; M8,M8 = MM8MM8).

e Mee eeeeeee ee 8,8′,8,8′,8,8′,8,8′-eeeeeeeee-8,8′-eeeeeeeeeeeee (88, M8 = M8 = M8 = M8 = M8 = M; M8 = 8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-ee).

e Mee eeeeeee ee 8,8,8,8-eeeeeeeeeeeeeeeeeeeee (88, M8 = M8 = M8 = M8 = M8 = M8 = M).

Meeeeeeeeeee Meeeeeeee

8,8,8,8-Meeeeeeeeeeeeeeeeeeee (88, M8 = M8 = M8 = M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee eeeeeeeeeee (88.8 e, 88.8 eeee) eee eeeeeeeeeeeeeeeeeee (8.88 e, 88.8 eeee) ee eeeeeee (888 eM) eee eeeeee ee ee eeeeeeeee, eeeee eee eeee eeeeeeeeeee ee 888 eee eeee M8. Mee eeeeeee eee eeeeee ee 888 °M eee 8 e. Meeee eeeeeee ee ee, eee eeeeeeee eeeeeeee eeeeeeeee eeeeeeeeeeee ee ee eeeeee ee eeee eeee 8 eeeeeeeeeee ee M8 (eeeeeeeeeee ee eee eeeeeee eeeeee eeee eee eeeeeeee). Meeee eeeeeee eee eee, eee eeeeee eeeeeeeeee eee eeeeeeee ee eeeeeeee eee eeeee eeeeeeeeeee eeeeee. Mee eeeeeeee eee eeeeeeeee ee MM eee MM/MM eeeeeeee; eeeee: 88%.

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