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20.2.1.4.1.2.3 Variation 3: Of Benzyl Halides

DOI: 10.1055/sos-SD-020-00102

Evano, G.Science of Synthesis, (200720147.

Transition-metal-catalyzed carboxylation with carbon monoxide is one of the most useful methods for the direct synthesis of phenylacetic acids 25 from benzyl halides 24 (Table 6). Many catalysts have been reported to be effective for the conversion of benzyl halides 24 into the corresponding carboxylic acids 25. Early catalytic systems were based either on palladium or iron; representative and most significant results obtained with these systems are collected in Table 6.[‌39‌‌42‌] These methods suffer, however, from the formation of byproducts resulting from reduction or dimerization and are strongly substrate-dependent.

Meeee 8 Meeeeeeee- ee Meee-Meeeeeeee Meeeeeeeeeeee ee Meeeee Meeeeee[‌88‌‌88‌]

Me8 M Meeeeeee Meeeeeeeeee Meeee (%) Mee
8-Mee Me Me(eeee)8 M 88 [‌88‌]
8-Mee Me Me(eeee)8 M 88 [‌88‌]
8-MM8M8 Me Me(MMe8)8 M 88 [‌88‌]
Me Me Me(MMe8)8 M 88 [‌88‌]
8-eeeeeeee Me Me(MMe8)8 M 88 [‌88‌]
Me Me MeMe8(MMe8)8 M 88 [‌88‌]
8-eMeM8M8 Me MeMe8(MMe8)8 M 88 [‌88‌]
Me Me Me(MM)8 M 88 [‌88‌]
Me Me Me(MM)8 M 88 [‌88‌]
8-Mee Me Me(MM)8 M 88 [‌88‌]
8-Mee Me Me(MM)8 M 88 [‌88‌]
8-MeM8M8 Me Me(MM)8 M 88 [‌88‌]
8-eeeeeeee Me Me(MM)8 M 88 [‌88‌]

e Meeeeeeeee M: MM (8 eee), MeMM, MM8Me8, M8M; M: MM (8 eee), [Me(MM8)8]8MMMM8, MeMM, MM8Me8, M8M; M: MM (8 eee), [Me(MM8)8]8MMMM8, MeMM, eeeeeee, M8M; M: MM (8 eee), MMMM, MeMM, e-eeeeee, M8M; M: MM (88 eee), MMMM8, MMe, MMM, M8M; M: MM (8 eee), Me8MMMM8, MeMM, MM8Me8, M8M; M: MM (88 eee), Me8MMMM8, MeMM, eeeeeee, M8M.

Me 8888 Meeee eee ee-eeeeeee eeeeeeee ee ee eeeeeeeeeee eeeeee eee eee eeeeeeeeeeeee ee eeeeee eeeeeee, eeeee eeee eeeee eeeee eeeee-eeeeeeee eeeeeeeeee, eee eee eeeeeeee ee e eeeeeeeeee eeee eee eeeeeeeee ee eeeeee(MM) eeeeeee.[‌88‌] Meeeeeee ee (eeeeeeeeeeee)eeeeee 88 eeee eeeeee(MM) eeeeeee eee eeeeee(MMM) eeeeeeee eeeee eeeee-eeeeeeee eeeeeeeeee ee 88°M, eee eeeee ee eeeeeeeeee ee eeeeee eeeeeeee eeee eeeeeeeeee eeeee 88 ee eeee eeeeee (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeeeee-Meeeeeee eee Meeeee(MM) Meeeeee Meeeeeeee Meeeeeeeeeeee ee (Meeeeeeeeeee)eeeeee eeeee Meeee-Meeeeeee Meeeeeeeee[‌88‌]

Meeeeeeeeee 8

Me8 Meeee (%) Mee
Me 88 [‌88‌]
8-MeM8M8 88 [‌88‌]
8-MeM8M8 88 [‌88‌]
8-Mee 88 [‌88‌]
8-Mee 88 [‌88‌]
8-eeeeeeee 88 [‌88‌]
8-eeeeeeee 88 [‌88‌]

Meeeeeeeeeeeeeeeeeeeee(8) [Me(MM)8] ee e eeee eeeeeeeee eeeeeeee eee eee eeeeeeeeeeeee ee eeeeee eeeeeee (Meeee 8). Meee eeeeeee eeeee eeee eee eeeeee(MM) eeeeeeee/eeeeee eeeeeeeeeee/eeeeee eeeeeeeee eeeeeee eeeeee (Meeee 8, Meeeee M),[‌88‌] ee eeeeeeeeeeee ee eeeeeeeeeeeeeeeeee (Meeee 8, Meeeee M),[‌88‌] ee ee eeee ee eee eeee ee eeeeee eeeeeeeeeeeeeeeeeeeeee(8) (Meeee 8, Meeeee M).[‌88‌] Me eee eeeee, eeeeeeeeee eeeee 88 eee eeeeeeee ee eeeeeeeee eeeeee eeeee eeeeeeeeee eeee eeeeeeee eeeeeeeeee (Meeee 8). Meeeeeee ee eeeee-eeeeeeee eeeeeeeee eee eeeee eee eeeeeeeee ee eee eeeeeee eeeeeeeeee eeeee. Meee eeee eeeeee eeeeeeee 88 (M=Me), eeee eeeee ee eeeeeeeeeee eeeeeeeeeeee eeeeeeeeeeee, eee ee eee eeeee eeeeee eeeeeeee eeeeeeeee eee eeee eeeeeeee.

Meeee 8 Meeeeeeeeeeee ee Meeeee Meeeeee Meeeeeeee ee Meeeeeeeeeeeeeeeeeeeee(8)[‌88‌‌88‌]

Me8 M8 M Meeeeee Meeee (%) Mee
Me M Me M 88 [‌88‌]
8-MeM8M8 M Me M 88 [‌88‌]
8-Mee M Me M 88 [‌88‌]
Me M Me M 88 [‌88‌]
Me 8-Mee Me M 88 [‌88‌]
Me Me Me M 88 [‌88‌]
Me 8-MeM8M8 Me M 88 [‌88‌]
8-eMeM8M8 Me Me M 88 [‌88‌]
Me Me Me M 88 [‌88‌]
Me Me Me M 88 [‌88‌]
Me Me Me M 88 [‌88‌]
8-MeM8M8 Me Me M 88 [‌88‌]

e Meeeee M: MM (8 eee), MeMe8/MeMM8/MeMM, MMM, M8M, 88°M; M: MM (8 eee), MeMe(MM)8, MeMM, MeMM, M8M, 88°M; M: MM (8 eee), Me8(MM)8, MMM, MeMM, M8M, 88°M.

Meeeeee eeeeeeeee eeee eeeeeee ee eeeeeeeee eeeeeeeeee-eeeee eeeeeeeee ee eeeeeeeeeeeee eeeeeeeee. Mee eee ee e eeee eeeee eeeeeeee ee eee eeeeeeee ee e eeeeeee eeeeeeee eee eeee eee eeeeeee ee eeeeeee eeeeeeeeeeee, eee eee eeeeeeee ee e eeeee-eeeeeeee eeeeeeee ee eee eeeeeeee ee ee eeeeeeeee eeee eee eeeee ee eeeeeeee eeeeee. Meeeeee, eeee eeeeee eeeeeeee eee eeeee ee eee eeeee eeeeeee, eeeee eee eeeeeeeeeeeee eeee ee eeeee eeeeeee ee eee eeeee. M eeeee eeeeeeeeeeee ee eeee eeeee eee eeeeeeee ee 8888: Meeeee eee ee-eeeeeee eeeeeeeeeeee eeee eeeeeeeeee eeeee 88 eeeee ee eeeeeeee ee eeeeeeeee eeeeee eeee (eeeeeeeeee)eeeeee 88 eeeee eeee eeeeeeeeee ee eeeeeeeeeeeee eeeeeeeee ee e eeeeeee eeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeee (Meeee 8).[‌88‌] Mee eeee eeeeeeee ee eeee eeeeeeeee ee eee eeeeeee eeee eeeeeeeee (Meeee 8, eeeeeee 88, 88).

Meeee 8 Meeeeee-Meeeeeeee Meeeeeeeeeeee ee (Meeeeeeeee)eeeeee[‌88‌]

Meeee Me8 M Meee (°M) Meeee (%) Mee
8 Me Me 88 88 [‌88‌]
8 8-e-MeM8M8 Me 88 88 [‌88‌]
8 8-MeM8M8 Me 88 88 [‌88‌]
8 8-MeM8M8 Me 88 88 [‌88‌]
8 8-MeM8M8 Me 88 88 [‌88‌]
8 8-MeM8MM8M8 Me 88 88 [‌88‌]
8 8-MMM8M8 Me 88 88 [‌88‌]
8 8-MM8M8 Me 88 88 [‌88‌]
8 8-MeMM8M8 Me 88 88 [‌88‌]
88 8-M8MM8M8 Me 88 88 [‌88‌]
88 8-MeM8M8 Me 88 88 [‌88‌]
88 Me Me 88 88 [‌88‌]
88 8-eeeeeee Me 88 8 [‌88‌]
88 Me 88 8 [‌88‌]

Meeeeeeeeeee Meeeeeeeee

Meeeeeeeee Meeee 88; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

MMMMMMM: Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

M eeee ee Me(MM)88M8M (888ee, 8.8eeee) eee MeMe88M8M (888ee, 8.8eeee) ee 8M ee MeMM (88eM) eee eeeee ee e eeeeeee (88eM) eeee eeeeeeeeee Me(MM8)88MMe8+Me (88ee, 8.888eeee) eee eee (eeeeeeeeeeee)eeeee 88 (88eeee). Mee eeeeeee eee eeeeeee eeeee MM (8 eee) ee 88°M eee 88e (eee eeeeeee eeeee eeeeee eee eeeee ee. 8e). Me eee eeee eeeeee ee ee, eee eeeeee eeee eeeeeeeee, eee eee eee eeeee ee eee eeeeeee eeeee, eeeee eee eeeeeeeee eeeeeeeee eeee 88% MMe eee eeee eeeeeeeee eeee Me8M (8×88eM). Mee eeeeeeee Me8M eeeeeeee eeee eeeeee eeee M8M (88eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee.

(8-eeee-Meeeeeeeeee)eeeeee Meee (88, Me8=8-e-MeM8M8); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

M eeeee eeeeeee eeee eeeeee eeeeeee 88 (Me8=8-e-MeM8M8; M=Me; 888ee, 8.8eeee), MM (88ee, 8.888eeee), eee Me8Me8(eee)8 (88ee, 8.888eeee) ee MMM8M (8eM) eee eeeeeee eeee M8 eee eeee eeeeee eeeee e MM eeeeeeeeee (8 eee) eee eeeeeee ee 88°M eee 88e. Meeee eee eeeeeee eee eeeeee ee ee, ee eee eeeeeeeeeeee, eeeeeee eeee MeMMe, eeeeee eeee 8M MMe eee eeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee); eeeee: 888ee (88%).

References