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1.1.1.2.2.1 Coupling of Arenes with Haloarenes

DOI: 10.1055/sos-SD-217-00003

Melkonyan, F. S.; Gevorgyan, V.Science of Synthesis: Catalytic Transformations via C—H Activation, (2015157.

Palladium(0)-catalyzed C—H arylation of [1,1′-biphenyl]-2-ols 141 and 144 with aryl iodides 142 and 145, respectively, affords the products of monoarylation 143 in the former case and the corresponding products of diarylation 146 in the latter (Scheme 48).[‌138‌] The selectivity of the transformation regarding mono- and/or diarylation products is controlled by the choice of palladium catalyst. Thus, the use of palladium(II) acetate (5 mol%) is efficient for the synthesis of [1,1′:2′,1′′-terphenyl]-2-ols 143, whereas employment of palladium(II) chloride leads to the 6′-phenyl-[1,1′:2′,1′′-terphenyl]-2-ols 146. The substituent scope for the [1,1′-biphenyl]-2-ols employed allows groups of different electronic nature to be used at the meta- and para-positions of the non-hydroxylated aryl ring, with substitution at the meta-position delivering only the products of monoarylation. Furthermore, the range of aryl iodides used is quite wide, including electron-donating and mildly electron-withdrawing groups at the meta- and para-positions.[‌139‌,‌138‌]

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M8 M8 M8 M8 Meeee (%) Mee
M M M M 88 [‌888‌]
M M MMe M 88 [‌888‌]
M M M MMe 88 [‌888‌]
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M MMe M M 88 [‌888‌]
M MM8 M M 88 [‌888‌]

Meeeeeeeeee 88M

M8 M8 Meeee (%) Mee
M M 88 [‌888‌]
M MMe 88 [‌888‌]
M Me 88 [‌888‌]
Me M 88 [‌888‌]

8-Meeeeeeeeeeeee-8-eee 888 eee ee eeeeeeeeeee eeeeeeeeeee eeee eeeeeeeeee-8-eee 888 eee eeeeeeeee(8)-eeeeeeeee M—M eeeeeeeee eeee eeee eeeeeee 888 (Meeeee 88).[‌888‌] Mee eeeeeeee ee eeeeeeeee ee eeeeeeeee(MM) eeeeeeee (8.8 eee%) eee eee eee ee eeeeee eeeeeeeee ee eeeeeeee ee ee eeee eeeeeeeee, ee eee eee ee eeeeeeeee eeeeeeeee ee ee eeeeeeeeeee eeee eeeee eee eeee eeeeeeee eeeeeeeeee eeeeeeee eeee eeeee eeeeee ee eee eeeeeee. Meee eeeeeeeeeeeeee ee eeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeee-8-ee (888, M8 = M) eee eee 8-eeeeeee-eeeeeeeeeee eeeeeeee 888 (M8 = MMe). Mee eeeeeeeeeee eeeee eee eee eeee eeeeeee 888 ee eeeee eee eeeeeeee eeeeeeeeee eeeeee ee eeeeeeeee eeeeeeeeee eeeeee ee eee eeee-eeeeeeee. Mee eeeee ee eee eeeeeeee eeeeee eeee eeee ee eeeeeeeee eeeee, eeeee eeee eee eeeeeeeeee ee eeee eeeeeeeeeeeeee, eeeee ee eeee eeeeeeeee.

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Meeeeeeeeee 88

M8 M8 Meeee (%) Mee
M M 88 [‌888‌]
M MMe 88 [‌888‌]
M Me 88 [‌888‌]
M Me 88 [‌888‌]
MMe M 88 [‌888‌]

Meeeeeee M—M eeeeeeeee ee eeeeeee 888 eeee eeee eeeeeeee 888 eeeeee ee ee eeeeeeeee eeeeee eee eee eeeeeeeee ee eeeeeeeeeeee eeeeeee eeee ee 8′-eeeeee-[8,8′:8′,8′′:8′′,8′′′:8′′′,8′′′′-eeeeeeeeeeeee]-8′′-eee 888 (Meeeee 88).[‌888‌] Mee eeeeeeeeeeeeee eeeeeeee eeeeeee eeee eeeeeeeeee M—M eeeeeeeee eeeeeeeee eeeee eee eeeeeee eeeeee M—M eeeeeeeee ee eee eee eeeee-eeeeeeeee ee eeeeee 888 ee eeeeeeee ee eeeee eeeeeeeeee M—M eeee eeeeeeeeee eeeeeeee ee eee eeeeee eeeeeee eeeee. Mee eeeeeee ee eeeeeeeee ee eeeeeeeee(MM) eeeeeee (8 eee%) ee eeeeeeeeeee eeee eeeeeeeeeeeeeeeeee ee eee eeeeee, eeeee eeeeeeeeee eeee eeeeeeeeee, ee eeeeeee eee ee eeee eeeeee ee eee eeeeee eeeeeeee.

Meeeee 88 Meeeeeeee ee 8′-Meeeee-[8,8′:8′,8′′:8′′,8′′′:8′′′,8′′′′-eeeeeeeeeeeee]-8′′-eee eee Meeeeeee M—M Meeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee (%) Mee
M M M 88 [‌888‌]
M e-Me M 88 [‌888‌]
M Me M 88 [‌888‌]
M M Me 88 [‌888‌]
M M M 88 [‌888‌]
MMe M M 88 [‌888‌]

Mee 8,8,8-eeeeeeeeeeeeee eeeeeeeeeeeee 888 eeeeeee eeeeeeeee(8)-eeeeeeeee M—M eeeeeeeee eeee eeee eeeeeeeee 888 ee eeeeee eee eeeeeeee ee eeeee-eeeeeeeeeeeee, eee 8-eeeeeeeeeeeeeeeee 888. Meeee eee eee ee eeee eeeeeeeee ee eeeeeeeee eee eeeeeeeee eeeeeeeeeeeee, eee eeeeeeeeee ee eeee eeeeeeee 888 eeee eeeeeeeeeeee (888) eeeeeee ee eeeeeeeee ee eee eeeeeeeeeee eeeeeeee, eee 8,8-eeeeeeeeeeeeeeeeeee 888 (Meeeee 88).[‌888‌,‌888‌] Meee eeeee ee eeeeeeeee eee eeeeeeeee ee e eee eeeeeee ee eeeeeeeee(MM) eeeeeee (8 eee%) ee eeeeeeeeeee eeee M-eeeeeeeeeeee eeeeeee eeeeeeeee 888 (8 eee%). Mee M—M eeeeeeeee ee eeeeeeeeeeee eeeeeeeee eee eeee eeee eeeeeeee.

Meeeee 88 Meeeeeeee ee 8-Meee- eee 8,8-Meeeeeeeeeeeeeeeeee ee M—M Meeeeeeee ee Meeeeeee Meeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee (%) Mee
M M Me 88 [‌888‌]
MMe MMe Me 88 [‌888‌]
MMe MMe MMe 88 [‌888‌]
MMe MMe MMe 88 [‌888‌]
M MMe8 Me 88 [‌888‌]

Meeeeeeeeee 88M

M8 Meeee (%) Mee
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Me 88 [‌888‌]

Meeeeee 8,8-eeeeee-M-eeeeeeeeeeeeeeee eee ee eeeeeeeeeee eeee M-eeeeeeeeeeeeeeee eee e eeeeee M—M eeeeeeeee. Mee eeeeeeee ee eeeeeeeee ee e eeeeee eeeeeeeee(MM) eeeeeee/eeeeeeeeeeeeeeeeee eeeeeeeee eeeeee eeeee eeeeee eeeeeeeee ee e eeee. Meeee eeeeeeeee eeee eeeeeeeeeeeeeeeeeeeeeeeeee ee eeee eeeeeeeee (eee Meeeeee 8.8.8.8.8.8) eee eeeee ee eee eeeeeee eeee eeeeee eeeeee, eee eeeeeee ee eee eeeeeeeeee ee ee eeee eeeeeee eee eeeeeeeeeeee eeee eeeeeeee. Me eeee eeeeeee, M-eeeeeeeeeeeeeee (888) eeeeeeeee eeeeeeee eeee 8-eeeee-8-eeeeeeeeeeeee (888) ee eeee 8,8-eee(8-eeeeeeeeeeee)-M-eeeeeeeeeeeeeee (888) ee 88% eeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee 8,8-Mee(8-eeeeeeeeeeee)-M-eeeeeeeeeeeeeee[‌888‌]

8-Meeeeeeeeee eeeee 888 eee 8,8-eeeeeeeeeeeee eeeee 888 eee ee eeeeeeeeeee eee M—M eeeeeeeee ee eeeeeee eeeee 888 eee 888 eeee eeee eeeeeeeee 888 eee 888, eeeeeeeeeeee (Meeeee 88).[‌888‌] Mee eeeeeeee ee eeeeeeeee ee eeeeeeeee(MM) eeeeeee (8 eee%) ee eeeeeeeeeee eeee eee eeeee, eeeeeeee-eeee ee-8-eeeeeeeee(eeeee)eeeeeeeee (888; 88 eee%) ee eee eeeeee. M eeeeeee ee eeeeeee eeeee eeeeeeeeee eeeeeeeeeeee ee eeeeeeeee eeeeeeeeee eeeeee ee eee eeeee-, eeee-, eee eeee-eeeeeeeee eee ee eeee eeeeeeeeeee ee eeee eeeeeeee. Me eeeeeee, eee eeeeeeeeee 888 eeeeeee eeeeeee eeeeeeeeeeee ee eee eeee-eeeeeeee, eeeeeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeee 888 eeee eeee eeee eeeee-M—M eeeeee eee eeeeeeeee. Meee ee ee eee eeeeeeeee eeee eee eeeeeeeeee eeeeeeee eeeeeeeeeee ee eee M—M eeeeeeeee eeeeeeee eeeeee eeeeee eeeeeee (eeee eeeee). Meee e eeeee eeeeeeeeeee, eeee ee eeeeeeee, ee eeeee ee eee eeee-eeeeeeee ee eee eeeeeeeee 888 (eee eeee eeeee-eeeeeeeee eee eeeeeeeee), eeee eeeeeeeeeeeeee eeeeeeee eee eeeeeeee ee eeeeeeeeeee 888. Mee eeeee ee eeee eeeeeeeee 888 eee 888 eeeeeee eee eee eeeeeee ee eeee eeeee eeeee eee, eeeeeee, eeeeeeeeeee eee eeee eeeee eee eeee eeeee ee eee eeeeeeee, eeee eeeeeeee eee eeeee ee e eeeeeeeee eeeeee eee eee eeeeeeeee ee eeee 8-eeee-, eee 8,8-eeeeeeeeeeeee eeeee.

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Meeeeeeeeee 88

M8 M8 M8 M8 Meeee (%) Mee
MM8 M M M 88 [‌888‌]
MM8 M Me M 88 [‌888‌]
MM8 M M M 88 [‌888‌]
MM8Me M M M 88e [‌888‌]
M Me MM8 M 88 [‌888‌]
M Me M Me 88 [‌888‌]

e Meeee eeeee eeeeeeeeee eeeeeeeeeeeeee eeee eeeee(eeeeeeeeeeeeee)eeeeeee.

Meeeeeeeeee 88M

M8 M8 M8 Meeee (%) Mee
M M M 88 [‌888‌]
M M MM8 88 [‌888‌]
M M Me 88 [‌888‌]
M M MM8 88 [‌888‌]
MM8 M MM8 88 [‌888‌]
MM8Me M MM8 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

[8,8′:8′,8′′-Meeeeeeee]-8-ee (888, M8 = M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[‌888‌]

M 888-eM, eee-eeeeee eeeee eee eeeeeee eeee Me8MM8 (8.8 eeee) eeeee eee eeee eeeee ee 888 °M ee eeeee eee 8 e. Me(MMe)8 (8.88 eeee), eeeeeeeeeee (888, M8 = M8 = M; 8.8 eeee), [8,8′-eeeeeeee]-8-ee (888, M8 = M8 = M; 8 eeee), 8-Å eeeeeeeee eeeeee (888 ee), eee MMM (8 eM) eeee eeee eeeee, eee eee eeeeeeeee eeeeeee eee eeeeeee ee 888 °M eee 88 e eeeee M8, eeeeeee ee eeee, eeeeeeeee eeee Me8M, eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeeee ee ee eee ee eeeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88%.

8-Meeeeeeeeeeeeeeee-8-ee (888, M8 = M8 = M); Meeeeee Meeeeeeee:[‌888‌]

M 888-eM, eee-eeeeee eeeee eee eeeeeee eeee Me8MM8 (8 eeee), eeeee eee eeee eeeee ee 888 °M ee eeeee eee 8 e. MeMe8 (8.888 eeee), eeeeeeeeeee (888, M8 = M; 8.8 eeee), eeeeeeeeee-8-ee (888, M8 = M; 8 eeee), eee MMM (8 eM) eeee eeee eeeee, eee eee eeeeeeeee eeeeeee eee eeeeeee ee 888 °M eee 88 e eeeee M8, eeeeeee ee eeee, eeeeeeeee eeee Me8M, eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeeee ee ee eee ee eeeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88%.

8′-Meeeee-[8,8′:8′,8′′:8′′,8′′′:8′′′,8′′′′-eeeeeeeeeeeee]-8′′-ee (888, M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[‌888‌]

M eeeee eee eeeeeee eeee eeeeeeeeeeee (888, M8 = M; 8.88 e, 8.8 eeee), eeeeee (888, M8 = M8 = M; 88 ee, 8.8 eeee), Me(MMe)8 (88.8 ee, 8.888 eeee), Me8M (88 ee, 8.88 eeee), Me8MM8 (8.88 e, 8.8 eeee), eee e-eeeeee (8 eM). Mee eeeeeeeee eeeeeee eee eeeeeee ee eeeeee (888 °M) eee 88 e eeeee M8, eeeeeee ee eeee ee ee, eeeeee eeee eeeeee MMe, eeeeeeeee eeee Me8M, eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88.8:8.8); eeeee: 888 ee (88%); ee 888–888 °M.

8′-Meeeee-[8,8′-eeeeeeee]-8-eeeeeeeeeeee (888, M8 = M8 = M; M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

M eeeee Meeeeee eeeee eeeeeeee eeee e eeeeeeee eeeeeee eee eee eeeeeee eeee eeeeeeee 888 (M8 = M8 = M; 8.8 eeee), eeee eeeeeeee 888 (M8 = Me; 8.8 eeee), Me(MMe)8 (8.88 eeee), eeeeee 888 (8.88 eeee), Me8MM8 (8.8 eeee), eee eeeeeee (8 eM). Mee eeeeeeeee eeeeeee eee eeeeeee ee 88 °M eee 88 e eee eeeeeee ee eeee ee ee. Mee eeeeeeee eee eeee eeeeeeee ee eeeeeeee ee 8 M ee MMe, eee eeee eeeeeee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeee eee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) ee eeee eee eeeeeee; eeeee: 88%.

8′-Meeeee-8-(eeeeeeeeeeeeeee)-[8,8′-eeeeeeee]-8-eeeeeeeeee Meee (888, M8 = MM8; M8 = M8 = M; M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

M 8-eM eeee eeeeeeee eeee e eeeeeeee eeeeeee eee eee eeeeeee eeee Me(MMe)8 (8.8 ee, 8.888 eeee), eeeeeee eeee 888 (M8 = MM8; M8 = M; 88 ee, 8.88 eeee), eee 8-eeeeeeeeeeeee (888, M8 = Me; M8 = M; 888 ee, 8.8 eeee). Mee eeee eee eeeeeee eeee eeeee, eeeeee, eee eeeeee eeeeee e eeeeeeee eeeeee ee-8-eeeeeeeee(eeeee)eeeeeeeee (888; 88.8 ee, 8.88 eeee), Me8MM8 (888 ee, 8.8 eeee), 8-Å eeeeeeeee eeeeee (888 ee), eee eeeee MMM (8.8 eM) eeee eeeee. Mee eeeeee eeee eee eeeeeee eeee eee eeeeeeee, eeeeeee ee ee eee 8 e, eee eeeeee ee e eeeeeeeee eee eeee ee 888 °M eee 88 e. Mee eeeeeeeee eeeeeee eee eeeeeee ee eeee ee ee eee eee eeeeeeee eee eeeeeeee eeee 88% ee MMe (8 eM). Mee eeeeeeeee eeeeeeeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM) eee eee eeeeeee eeeeee eeee eeeeeeee eeeeeee e eee ee Meeeee. Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeee ee e eeeeee ee eeeee 8 eM eee eee eeeeeee eee eeeeeeee eeee eeeeee eee eee eeeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeeee eeee MM8Me8/MeMMe 88:8). Mee MM8Me8/MeMMe eeeeeeee eee eeeeeeeeeeee eee eee eeeeeee eeeeeeee eee eeeeeeeeee eeee eeeeeeeee M8M (8 × 8 eM) eee eeeee eeeee eeeeeee eeeeeeee. Meee eeeeeee eee eeeeeeeeee eeee eeeeeee (8 × 8 eM) eee/ee eeeeeeee ee eeeeeeeeeee MMMM eee eeeee eeeee eeeeeee eeeeeeee (88 °M) ee eeee eee eeeeeee (Me = 8.88, MM8Me8/MeMMe 8:8) ee e eeeee eeeee; eeeee: 888 ee (88%); ee 888–888 °M (eeeeeeeee).

References


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