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45.13.1.7.2.1 Variation 1: In the Presence of Directing Groups

DOI: 10.1055/sos-SD-045-00510

Black, D. A.; Fagnou, K.Science of Synthesis, (201045612.

A wide range of heteroatom-containing directing groups have been employed for regioselective ortho-directed arylation with aryl bromides and chlorides; thus, for example, 1,3-benzodioxole (174) undergoes arylation with 1-bromo-4-(trifluoromethyl)benzene in the presence of a palladium/phosphine catalyst to afford 4-[4-(trifluoromethyl)phenyl]-1,3-benzodioxole (175) in 86% yield (Scheme 64).[‌231‌]

Meeeee 88 Meeeeeeee ee 8,8-Meeeeeeeeeee[‌888‌]

Meeeeeee eee eeee eeeeeeeee eeeeeeeeee eee eeeeeeeee ee e eeeee ee eeeeeeeeeee eeee eeeeeeee eee eeeeeeeeeeeeeeeeeeeeeeeeee eee eeeeee eee eeeeeeeeeee eeeeeee 888 ee eeee eeeeee eeeeeeee eeeeeeee 888 (Meeeee 88). Mee eeeeeee, eeeeee eeeeeeeeeee ee eee eeeeeeeee 888 (M8=8-MMe; M=MMMMMe) eeeeee eeee ee ee eeeeeee eeee eeeeeee eeeeeeeeeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee(MM) eeeeeee eee eeeeeeeeeeeeeeeeee ee eeeeeee eeee eeeeee eeeeeeeee ee eeeeeee ee 888°M ee eeeeeee eeeeeeee 888 (M8=M; M8=8-MMe; M=MMMMMe).[‌888‌] M-Meeeeeeeeeeeeeee eee eeee ee eeee, eeeeeeee eee eeeeee eeeeeeeee eeeee ee eee eeeeeeee eeee.[‌888‌] Meeeeeee, e eeee eeeee ee eeeee eeeeee eee ee eeeeeeee ee eeeeeeee eeeeeeeee eee eeeeee eeeeeeeee,[‌888‌] ee eeee ee eeeeeeeeee eee eeeeeeee-eeee eee eeeeeeee-eeee eeeeeeeeee. Mee eeeeee eeeeeee eeeeeeeeeeee, eee 8-eeeeeeeeeeeee ee eeeeeeeeee eee eeeeeeeeeee eeeeeeee eee eeee eeeeeeeee ee eeeeeeeeee eeee eeeeeee[‌888‌] ee eeeeeeeee eeeeeeeee.[‌888‌,‌888‌] Meee eeeeeeee, eeeeeee, ee eee eeee eeeee eeee eeeeeeeeeeeee ee eeeeeee eeeeeeeeeee 8-eeeeeeeeeeeee eee ee eeeeeeeee eeeee eeeeeeeee eeeeeeeee eeeee eeeeeeee eeeee.[‌888‌] Meeeeeeee eeeeeeeee eeee eeeeeeee eeeeeeeee eeeeeee eeee eeeeeeee ee eeee 8-eeeeeeeeeeeeeeeee eee 8-eeeeeeeeeeeeeeeeeee eee eeee eee eeee ee eeeeee eeeeeeeeeee.[‌888‌,‌888‌] Meeeee, eeeee, eee eeeeeee eeeeeeeee eeee eee ee eeeeeeeee eeeeee ee eeeeeeeee-eeeeeeeee eeeeeeeeee, eee eeee eeeeeeeee eee eeee ee eee eeeeeeeee ee eeeeeeeeeeee eeeeeeeeeee eeee e eeeeee eeeeeeeeee eeeeeeeeee eeeeeeee-eeee eeeeeeee eeeeeeeeeeee eeeeeee eeeeeeeee eeeeeee ee eeeeeee.[‌888‌] Meeee eeeeee eee ee eeeeeeee eee eee eeeeeee ee eeeeee eeeeeeeeee eeeee eeeeeeeee eeeeeeeee,[‌888‌,‌888‌] eee eeee eeeeeeeee ee eeeeeeeeeeee eeeeee ee, eeeee eee eeeeeeee eeee, eee eeeee eeeeeeee eee ee eeeeeee eeeeeeeee eeee e eeeee ee eeeee eeeeee ee eeeeeeeeee eee eeeeeeeeee eeeeeeeee ee eeeeeeeee, ee eeeeee ee eeeeeeeee. Mee eeeee-eeeeeeeee ee eeeeeee ee eeee eeeeeeee eeeee e eeeeeee eeeeeeee eeee eeeeeeeee eeeeeeeeee ee eeeeeeeeeeeeeeeeeeeee eeeeeeee,[‌888‌] eeeeeeee eee eeeeeeeeeee eeeeee 888 eeeeeeeeee eeee eeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeee(M) eeeeeeee ee eeeeeeeee ee eee eeeeeeee ee 8-eeeeeeeeeeeeeeeee eeee 8-eeee-eeeeeeeeeee ee eeeeee eee eeeeee 888 (M8= 8-Me; M8=8-e-Me) (Meeeee 88);[‌888‌] eeee eeee eeeeeee eeeee eeee eee ee e eeeeee ee eeeee eeeeeeeeee ee eeee eeee.[‌888‌,‌888‌]

Meeeee 88 Meeeeeeeeeeeee Meeeee Meeeeeeee eeee Meeeeeeeeeee Meeeeeeee Meeeee[‌888‌‌888‌,‌888‌,‌888‌‌888‌]

Meeeeeeeeee 88

M8 M M8e M Meeeeeeeee Meeee (%) Mee
M MMe 8-MMe MMMMMe Me(MMe)8 (8eee%), Me8M (88eee%), Me8MM8, eeeeeee, 888°M 88e [‌888‌]
8-Me M M MMMMe-Me Me(MMe)8 (8.8eee%), MeMMe, MMM, 88888°M 88e [‌888‌]
M M+(Mee) MM8 8-MMe Me(MMe)8 (8eee%), MeMMe, MeMM, 888°M 88e [‌888‌]
M M+Me MM8 8-Me Me(MMe)8 (8eee%), MeMM, 888°M 88e [‌888‌]
M Me M Me8Me8(η8-M8M8)8 (8.8eee%), Me8M (88eee%), M8MM8, MMM, 888°M 888e [‌888‌]
8-MMe Me 8,8,8-(MMe)8 MMM Me(MMe)8 (8eee%), eeeeee 888 (8.8eee%), Me8MM8, eeeeeee, 88°M 88e [‌888‌]
8,8-(MM=MM)8 Me 8-Me Me8Me8(η8-M8M8)8 (8.8eee%), Me8M (88eee%), M8MM8, MMM, 888°M 88e [‌888‌]
M Me 8-MM8 MM Me8Me8(eee)8 (8.8eee%), MMMM (88eee%), M8MM8, eeeeeee, 888°M 88e [‌888‌]
8-Me Me 8-e-Me MM MeMe(MMe8)8 (8eee%), eeeeee 888 (88eee%), Me8MM8, eeeeeee, 888°M 88e [‌888‌]

e Meeeeeee ee eeeeeeee eeeeeeee 888.

e Mee eeeeeee ee eee eeeeeeeeeee eeeeeeeeee eeeeeeee 888.

e Mee eeeeeee ee eee eeeeeeeeeee eeeeeeeeeeee eeeeeeee 888.

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

Meeeee 88 Meeeeeeeeeeeee Meeeee Meeeeeeee eeee Meeeeeeee Meeeee[‌888‌‌888‌]

Meeeeeeeeeee Meeeeeeee

8-[8-(Meeeeeeeeeeeeee)eeeeee]-8,8-eeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Meeeeee M8MM8 (8eeeee), MeMMe (8eeeee), Me(MMe)8 (8.88eeeee), eee e-Me8MeMMMM8 (8.88eeeee) eeee eeeeee ee e 88-eM eeee eeeeeeee eeee e eeeeeeee eeeeeee eee. Mee eeee eee eeeeee ee e Meeeeee Meeeeeee Meeeeeeeeee, eeeee eee eeeeee eeee eeeee. 8-Meeee-8-(eeeeeeeeeeeeeee)eeeeeee (8eeeee) eee 8,8-eeeeeeeeeeee (888; 88eeeee) eeee eeee eeeee eee e eeeeeee eee eeeeeeee MMM (8.8eM) eee eeeeeeeeee. Mee eeeeeee eee eeeeee ee 888°M eeeeeeeee eee, eeee eee eeeeeeee eee eeee (MMM ee MM/MM), eee eeee eeeeee eee eeeeeee, eee eee eeeeeee eee eeeeeee ee eeee. Mee eeeee eeeeeee eee eeeeeee eeee MeMMe, eeeeeeee eeeeeee e eeee ee Meeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeee e eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee/eeeeeee); eeeee: 88%; ee 8888°M.

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

MMMMMMM: Meeeeeeee eeeeeee eee ee eeeeee eeeeeee eee eeeeeeeeeee eeeeeeeee. Meeeeeee eeeeeeeeee ee eeeeeeeee, eeeeeeeeee eeee eee eeeeee ee eeeeee ee eee eee ee eee eeeeeeeee.

8-[8-(8-Meeeeee)eeeeee]eeeeeeee (888ee, 8.88eeee), [Me8M]MM8 (888ee, 8.88eeee), Me(MMe)8 (8.888eeee, 8eee%), eee MeMM (8eM) eeee eeeeee ee e 88-eM eeee. Mee eeee eee eeeeee eeee e Meeeee-eeeee eee eee eee eeeeeee eee eeeeee ee 888°M eee 8e, eeeeee ee eee eeeeee eee eeeeeeee eeeeeee e eeee ee Meeeee. Mee eeeeeee eee eeee eeeeeee eeee eee eeeeeeee ee eeeee ee eee eeee eee eeeeeeeeeee ee MM8Me8 eee eeeeeeeee ee eeee eeee eee. ee MeMMM8 (8 × 88eM) eee eeeee (8 × 88eM). Mee eeeeeee eeeee eee eeeeeeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee ee eeeeee ee eeeeee eee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/MeMMe 88:88) ee eeee ee eeeeee/eeeee eeeee; eeeee: 888ee (88%); ee 8888°M.

8,8,8,8-Meeeeeeeeeeeeeeeeeee-8-eeeeeeeeeeee [888, M8=8-MMe; M8=8,8,8-(MMe)8; M=MMM]; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeee eeeeeee eee ee eeeeee eeeeeee eee eeeeeeeeeee eeeeeeeee. Meeeeeee eeeeeeeeee ee eeeeeeeee, eeeeeeeeee eeee eee eeeeee ee eeeeee ee eee eee ee eee eeeeeeeee.

M eeeee Meeeeee eeeee eeeeeeee eeee e eeeeeeee eeeeeee eee eee eeeeeee eeee 8,8,8-eee­eeeeeeeeeeeeeeeeeee (888ee, 8.8eeee), 8-eeeeeeeeeeeee (888.8ee, 8.8eeee), Me(MMe)8 (8.88eeee), eee eeeeee 888 (8.88eeee), Me8MM8 (8.8eeee), eee eeeeeee (8.8eM). Mee eeeeeee eee eeeeee ee 88°M eee 88e, eee eeeee eeeeeee ee ee, eee eeeeeeee eee eeeeeeee ee eee eeeeeeee ee 8M MMe. Mee eeeeeee eee eeeeeeeee eeee Me8M eee eee eeeeeeee eeeeeeee eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 8:8); eeeee: 888ee (88%).

8-Meeeeee-M-{8-[8-eeeeee-8-(8-eeeeeeee)eeeeee]eeeeeeeeee}eeeeeee [888, M8=8,8-(MM=MM)8; M8=8-Me; M=(8-MeMM8M8)M=MMe]; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeee eeeeeee eee ee eeeeee eeeeeee eee eeeeeeeeeee eeeeeeeee. Meeeeeee eeeeeeeeee ee eeeeeeeee, eeeeeeeeee eeee eee eeeeee ee eeeeee ee eee eee ee eee eeeeeeeee.

M eeeeeee ee 8-eeeeeee-M-[8-(8-eeeee)eeeeeeeeee]eeeeeee (888ee, 8.8eeee), 8-eeeeeeeeeeeeeeee (888ee, 8.8eeee), M8MM8 (8.8eeee), Me8M (8.88eeee), eee Me8Me8(η8-M8M8)8 (8.8888eeee) ee eeeee MMM (8eM) eeee eeeeee ee e Meeeeee eeee eee eeeeee eee eeeeeee ee 888°M eee 88e eeeee M8. Mee eeeeeee eee eeee eeeeee eee eeeeeee eeee Me8M (88eM), eeeeee eeee M8M (8 × 88eM), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 8:8); eeeee: 88%.

8-(8-eeee-Meeee-8-eeeeeeeeeeeeeee-8-ee)eeeeeeee (888, M8=8-Me; M8=8-e-Me; M=MM); Meeeeee Meeeeeeee:[‌888‌]

MeMe(MMe8)8 (8.88eeee), eee eeeeee 888 (8.88eeee), 8-eeeeeeeeeeeeeeeee (888ee, 8.88eeee), 8-eeee-eeeeeeeeeee (888ee, 8.88eeee), eee Me8MM8 (8.88eeee) eeee eeeeeeeee ee eeeeeee (88eM) eee eee eeee eee eeeeeeee eeeee M8 eee 88e. Meeee eeeeeee eee eeeeeee, 8MMMe (8eM) eee eeeee eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 × 88eM). Mee eeeeeeee eeeeeeee eeee eeeee (MeMM8) eee eeeeeeee, eee eee eeeeeee eee eeeeeee eeee eee eeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MMMe8/eeeeee 8:8) ee eeee e eeeeeeeee eeeee; eeeee: 888ee (88%).

M-(8,8-Meeeeeee-8,8:8,8-eeeeeeeee-8-ee)-8,8-eeeeeeeeeeeeeeeeeee (888, M8=8-Me; M8=M; M=MMMMe-Me); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeee eeeeeee eee ee eeeeee eeeeeee eee eeeeeeeeeee eeeeeeeee. Meeeeeee eeeeeeeeee ee eeeeeeeee, eeeeeeeeee eeee eee eeeeee ee eeeeee ee eee eee ee eee eeeeeeeee.

M eeee ee 8,8-eeeeeeee-M-eeeeeeeeeeeeeeeee (888ee, 8.8eeee), 8-eeeeeeeeeee (8.88e, 88.8eeee), Me(MMe)8 (8.888eeee), eee MeMMe (8.8eeee) ee MMM (8eM) eeeeeeeee ee e 8-eeee eeeee-eeeeee eeee eee eeeeee ee 88°M eee 8e. Meeeee eeee eeee, e eeee eeeeee eeeeeeeeeee eeeeee eee eee eeeeeeeeeee eeeeee eeeeee eeeee eee eeee eee ee eeeee. Meeee eeeeeee ee ee, eee eeeeeee eee eeeeeee eeee eeeeeee (88eM) eee eee eeee eee eeeeeeeee ee eeeeeeeeeee ee eeeee e eeeeeeeeeee eeee eee eeeeee eeee eeeeeee (8 × 8eM). Mee eeeeeeee eeeeeee eeeeee eeee eeee eeeeeeee eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee eeee MM8Me8/eeeeeee 8:8) ee eeee eee eeeee eeeeeeee ee e eeeeeeeee eeeee; eeeee: 888ee (88%); ee 888888°M.

8-Meeeee-8-eeeeeeeeeeeeeeeeeee-8(8M)-eee (888); Meeeeee Meeeeeeee:[‌888‌,‌888‌]

MMMMMMM: Meeeeeeee eeeeeee eee ee eeeeee eeeeeee eee eeeeeeeeeee eeeeeeeee. Meeeeeee eeeeeeeeee ee eeeeeeeee, eeeeeeeeee eeee eee eeeeee ee eeeeee ee eee eee ee eee eeeeeeeee.

M Meeeeee-eeee eeeee eee eeeeeee eeeee M8 eeee Me(MMe)8 (8.888eeee), eee(8-eeeee)eeeeeeeee (8.8ee, 8.888eeee), M8MM8 (8.88eeee), M-eeeeee-8-eeeeeeeeeeeeee (88.8ee, 8.88eeee), e eeee ee eeeeeeeeee (88.8ee, 8.888eeee) ee eeeee MeMM (8.8eM) eee 8-­eeeeeeeeeee (88ee, 8.88eeee). Mee eeeeeee eee eeeeee eeeee eeeeeeee ee 88°M eee 88e, eee eeee ee eee eeeeee ee ee. Meeee eee eeeeeeee ee eee. ee MM8Me (88eM) eee eeeeeeeeee eeee MeMMe (8 × 8eM), eee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eeeee (88eM) eee eeeee (Me8MM8). Meeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe) ee eeeeeee e eeeeeeeee eeeee; eeeee: 88ee (88%); ee 888888°M.

References


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