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Please login or sign up for a free trial to access the full content. Method 4: Metal-Catalyzed Cross Coupling

DOI: 10.1055/sos-SD-015-01146

Álvarez, M.; Joule, J. A.Science of Synthesis, (200515795.

The arrival of metal-catalyzed cross-coupling methodologies, particularly using palladium(0), has made a major impact on isoquinoline chemistry, as elsewhere. Most of the ­examples involve halo- or triflyloxy-substitution of the heterocyclic ring of isoquinolines. There are fewer examples involving halo-substitution of the benzene of iso­quinolines, but these include the conversion of 6-bromoisoquinoline into a 6-carbox­ylate by carbonylation using carbon monoxide, palladium(II) acetate in dimethylform­amide/methanol at 100°C[‌422‌] and arylation of several benzene-ring halides, including chlorides, using nickel catalysis to give 5-, 6-, 7-, or 8-arylisoquinolines 479 (Scheme 223).[‌423‌]

Meeeee 888 Meeee Meeeeeee ee eee Meee-Meeeeeeeeee Meeeeee Meee ee Meeeeeeeeeee[‌888‌]

Meeeeeeeeeeeeeeee eeeeee eeeeee eeee 8-eeee-8-eeeeeeeeeeeeeeeeee eeee eeeeeeeee eeeeee eeeeee eeeeeeeeeee eee eeeeeeeeeeeeeeeee eeeee ee M8 ee eeee 888 (Meeeee 888).[‌888‌] Meeeeeeeeee-8-eeeee (888) ee eeeeeeee, eeeeeeee eee ee eeee eeeeee, eeee 8-eeeeeeeeeeeeeeeee (888) ee eeeeeeee eeee eeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeee(MM) eeeeeee ee 888°M[‌888‌] ee eeeeee eeeee ee 888°M.[‌888‌]

Meeeee 888 Meeee Meeeeeee ee Meeeeeeeeeeeeeeee[‌888‌,‌888‌]

8-Meeeeeeeeeeeeeeeee ee eeeeeeeee eeee 8-eeeeee-, 8-eeeeee-, eee 8-[8-(eeeeeeeeeeeeeee)eeeeee]eeeeeeeeeeeee ee eeeeeeee eeee eee eeeeeeeeeeeee Meeeeeee eeeeeeee eeeee ee eee eeeeeeee [8,8-eee(eeeeeeeeeeeeeeeeee)eeeeeee]eeeeee(MM)[‌888‌,‌888‌] eee, ee eeee eeeeeeeeeee, 8-eeeee-8-eeeeeeeeeeeeeeeeee eeeeee eeee eeeeeeeeeeeeeee eeeeee eeeee eeeeeeee[8,8-eee(eeeeeeeeeeeeeeeeee)eeeeee]eeeeeeeee(MM) ee eeeeeeee eeeeeeeee 8-eeeee-8-eeeeeeeeeeeeeeeeee (888).[‌888‌] Mee [8,8-eee(eeeeeeeeeeeeeeeeee)eeeeeee]eeeeee(MM) eeeeee ee eeee eeee ee eeeeeee 8-eeeeeeeeeeeeeeeee eeee 8-eeeeeeeeeeeeeeeeee eeee eeeeeeeeeeeeeee eeeeee, eee ee eeeeee 8-eeeeee-eeeeeeeeeee 8,8-eeeeeeeeeeeeeeeeeeeee eeee eeee ee eeeee Meeeeeee eeeeeeee, e.e. ee eeee 888 (Meeeee 888).[‌888‌]

Meeeee 888 Meeeee- ee Meeeeeeee-Meeeeeeee Meeeeeee ee 8-Meeeeeeeeeeeeeeeeee eeee Meeeeeee Meeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee ee 8-eeeeeeeeeeeeeeeeeee ee eeee 8,8-eeeeeeeeeeeeeee 888 (Meeeee 888) ee eeeeeeee eeeee e eeeeee eeeeeeee eeeeee, ee eeee, ee eeeeeeeee ee eeeeee(MM) eeeeeeee eeeeeeeeeee eeee eeee.[‌888‌,‌888‌]

Meeeee 888 Meeeeeeeeeee ee 8-Meeeeeeeeeeeeeeeeee[‌888‌,‌888‌]

Me e eeeeeeeeee eeeeeeeee eeeeeee eeee eee eeeee eeeeeeeee, 8-eeeeeeeeeeeeeeeeee eeeeeee eeee eeeeeeeeeeeeeeeeeee eeeeeee ee eeee 8-eeeeeeeeeeeeeeeeeeeeee ee 88% eeeee eee eeee eeeeeeeeeeeeeee eeeeeee ee eeee 8-eeeeeeeeeeeeeeeeee ee 88% eeeee eeeee eeee(eee­e­eeeeeeeeeee)eeee ee 8-eeeeeeeeeeeeeeee-8-eee ee eeee eeeeeeeeeee eee 88 eeeeeee.[‌888‌]

Meeee eeeeeeeee ee 8-eeeeeeeeeeeeeeeeee eeeeeee eeeeeeee eeee eeeeeee(8-eeeeeee)eeeeee eeeee eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee eeee eeeeeeeeeeeeeeeeee eeeeeee eee eeeeeeeee eeeeeeeee eeeeee 8-(8-eeeeeee)eeeeeeeeeeee,[‌888‌] eeee (eeeeeeeeeeeeee)eeeeeeeee, eeeeeeeee 8-[(eeeeeeeeeeeeee)eeeeeee]eeeeeeeeeeee eeeee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee, eeeeee(M) eeeeee, eee eeeeeeeeeeeee ee e eeeeee eeee ee 88°M (8-eeeeeeeeeeeeeeee eeeeee ee 88°M); eee 8- eee 8-eeeeeeee eeee eeeeeeeee eeeeeee (Meeeee 888).[‌888‌] Meeee eeeeeeeeee (MMMMe, MMMMe, MMMMM8MM) eeeeee eeee 8-eeeeeeeeeeeeeeee eee 8-eeeee- eee 8-eeeeeeeeeeeeeeeee eeeee eee eeee eeeeee ee eeee eeeeeeee 888[‌888‌] eee 8-eeeeee-8,8-eeeeeeeee-8-eeeeeeeeeeeeeeeee eeeeeee eeeeeeeeeeee eeee (eeeeeeeeeeeeee)eeee­eeeee.[‌888‌] Meee 8-eeeeeeeeeeeeeeee ee eeeeeee eeee (eeeeeeeeeeeeee)eeeeeeeeee eeeeeee, e 8:8 eeeeeee ee eeeee eeeeeeeeeeee-8-eeeeeee eee 8,8-eeeeeeeeeeeeee ee eeeeeeee.[‌888‌]

Meeeee 888 Meeeeeee ee Meeeeeeeeeee Meeeeee eeee Meeeeeeeee[‌888‌,‌888‌]

Meeeeeee, ee eeeeeeeee eeeee, 8-eeeeeeeeeeeeeeeee eeee eeeeeeeeeee ee eeeeeeeee(8)-eeeeeeeee eeeeeeeee, eeeee ee e eeeeeeee eeeeeeeeee ee eeeeeeeeee eeeeeee 8- eee 8-eeee eeeeeeeeeeee. Meee 8,8-eeeeeee-[‌88‌] eee 8,8-eeeeeeeeeeeeeeeeeeeee[‌88‌] eeeee eeeeeeeeeee (Meeeee 888): eee eeeeee eeeeeee eeeeeeee eeee eeeeeeeee eeeeeee eee Meee eeeeeeee eeee eeeee eeeeeeee eeee ee M8, e.e. eeeeeeeee ee 888, eee eee eeeeee eeeeee eeee e eeeee ee eeee eeeeeee, eeeee eeee ee M8, e.e. eeeeeeeee ee 888. Mee, eeeee eeeeeee eeeeeeee, 8-eeeee-8-eeee­eeeeeeeeeeeeeee eeee eeeeee eeee eeeeeeeee eeeeeee ee eeee 888 eee eeeeeeeee Meee eeeeeeee eeee eeeee eeeeeeee,[‌88‌] eee 8-eeee-8-eeeeeeeeeeeeeeeeeee 888 ee eeeeee ee M8 eeee eeeeeeeeeee eeeee [Me(MMe8)8] ee eeee 8,8-eeeeeeeeeeeeeeeeeee 888, eeeeeeeeeeeee [Me(MMe8)8], ee eeee Meeeeeee eeeeeeee [MeMe8(eeee)] ee eeeeeee eeeeeeee(eeeeeeeeee)eeeeeeeeeee [MeMe8(eeee)].[‌88‌] 8-Meeeeeeeeeeeeeee-8-eeeee eeeeeee eeee (eeeeeeeeeeeeee)eeeeeeeee eeeee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee, eeeeeeeeeeeee, eee eeeeeeeeeeeeeeeee ee 888°M (88%) eee eee eeeeeeee eeeeeeeeee eeee eeee ee eee eeeeeeeee ee 8,8-eee[(eeeeeeeeeeeeee)eeeeeee]eeeeeeeeeee-8-eeeee ee 88% eeeee.[‌888‌]

Meeeee 888 Meeeeeeee Meeeeeee ee 8- eee 8-Meeeeeeeeeeeeeeee[‌88‌,‌88‌]

8-Meeeeeeeeeeeeeeee (888) eeeee eeee ee eee eeee eeeee ee eeeeeeeee(8)-eeeeeeeee eeeeeeee eeeeeeeee, eee eeeeeee eeee 8-eeeeeeeee-8-ee-8-ee eeeee eeeeeeeeeee(eeeeeeeeeeeee­eeeee)eeeeeeeee(MM), eeeeeeeeeeee ee eeee eeeeeeeeeee (88% eeeee),[‌888‌] eeee 8,8-eeeeee­eee-8-(eeeeeeeeeeeeeeeeeeee)eeeeeeeeeeeee eeee [Me(MMe8)8, Me8MM8, MMM, eeeeee] ee eeee 888 eeeee eeeeeeeeeeee (Meeeee 888),[‌888‌] eeee 8,8-eeeeeeee-8-(eeeeeeeeeeeeeeee)-8,8-eeeeeeeeeeeeee [Me(MMe8)8, eeeeeee, eeeeee; 88% eeeee][‌888‌] eeee eeeeee eeeeeeee [MeMe8(MMe8)8, MM (8.8eee), 888°M] eeeeee eeeee eeeeeeeeeeee-8-eeeeeeeeeee eeeeeeeeeeeeee,[‌888‌] ee Meee eeeeeeeee eeee eeeee eeeeeeee, eeeeeeeeeeeee, eee eeeeeee [Me(MMe)8, Me8M, Me8M, 888°M; 88, 88, 88% eeeee eeeeeeeeeeee][‌888‌] eee eeeeeeeee-eeeeeeeee Meeeee eee Meeeeee eeeeeeeee eeee eeeeeeee(8-eeeeeeeeeee)eeeeeeee eee 8-eeeeeeeeeeeeeee eeeeeeee, eeeeeee­eeeee, eeeeeee ee 8-eeeeeeeeeeeeeeeeee.[‌888‌] Mee 8- eee 8-eeeeeeeeeeeeeeeeeee eee eeeeeeee ee eeeeeeeeee eeeeeeeee eee eeeee eee 8- eee 8-eeeeeeeeeeeeeeeeeeeeeeeeee, eeeee eee eeeeeee eeeeeeee eeee eeeeeeeeeee-8(8M)-eee eee eeeeeeeeeee-8-ee, eeeeeeeeeeee.[‌888‌]

Meeeee 888 Me Meeeeee ee Meeee Meeeeeee ee 8-Meeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeeee (888, M8=8-Me); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeee-eeeee eeeeeeeee, MeMe8(eeee) (88ee) eee 8-eeeeeeeeeeeeeeeee (ee. 8e) eeee eeeeeeeee ee eee MMM (88eM). Mee Meeeeeee eeee (8.8 eeeee) eee eeeee eee eee eeeeeee eeeeeee ee ee eee 88e, eeee eeeeee eeee eeee eee MMe. Mee eeeeee eeee eee eeeeee eeee Me8M eeee eeee eeeee eeeee M8MM8 eee eeeeeeeee eeee Me8M. Meeeeeeeeee ee eee Me8M eeee 8-eeee­eeeeeeeeeeeeee; eeeee: 88%; ee (eeeeeeeeeeee) 888888°M.

8-(Meeeeeeeeeeeeeeee)-8-eeeeeeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Meeeeeeeeeeeeeeee eeeeee (88.8e, 88eeee), eeeeeeeee Me eeeeee (88e), eee MMMM (888eM) eeee eeeeee ee 88°M. Meeee ee eeeeeeeee eeeeee eeeeeeeee eeeeee ee eeeeee. 88°M, eee eeeeeeeeeee eee eeeeee ee 888°M eeee ee eeeeeeeeee eeeeeeee eeeeeeee. Meeee eeeeeeee eee ee eeeeeeeeee 8e, 8-eeee-8-eeeeeeeeeeeeeeeeee (88.8e, 88eeee) eee eeeee eee eee eeeeeee eeeeee eee eeeeeee eee e eeeeeee 8e. Mee eeeeeee eee eeeeee eee eee eeeeee eeeee eeee eeeeeeeeeeee eeeeeeeee ee eeeeeeeeee eee eeeeee eeee M8M. Mee MMMM eeee eee eeeeeee 8:8 eeee M8M eee eee eeeeeeeeeee eeee eeeeee eee eeeeeeeee ee eeeeeeeeee. Meee eeeeee eeee eeeeeeee, eeeee ee e eeeeee eeeeeeeeee, eee eeee eeeeeeee eee eeeeeeeeeeeeee [eeeeeeeee eeeee (ee 88888°M)]; eeeee: 8.8e (88%); ee 8888.8°M.

Meeeeeeeeee-8-eeeee (888); Meeeeee Meeeeeeee:[‌888‌]

8-Meeeeeeeeeeeeeeee (888; 88e, 8.88eee), eeeee MM8MM (888eM), eee MeMM88M8M (8e) eeee eeeeee eeeeeeee ee 888888°M eee 88e ee e eeeeeee eeeeeeeee. Mee MeMM eee eeeee ee eee eeeeeee eee eeee ee eee eeeeeeeee eeee eeeeeee (8×888eM) (MMMMMMM: eeeeeeeeee). Mee eeeeeeee eeee eeeee, eeeeeee eeee eeeeeeeeeeee eeeeeeee, eee eeeeeeeeeeee ee 88eM. Me eeeeeee, eeeeee ee eee eeeeeeeeeeeee eeee eeeeee; eeeee: 88e (88%); ee 888888.8°M.

8-Meeee-8-eeeeeeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee 8-eeeee-8-eeeeeeeeeeeeeeeeee (8.8e, 88.8eeee), MeMeM (88eeee), eee MeMe8(eeee) (888ee) ee Me8M (888eM) eee eeeeeeee eee 8e. Mee eeeeee Meeeeeee eeeeeee eee eeeeeeeeee ee eee eeeeeeee ee eee. MM8Me eee eee Me8M eeeee eeeeee eeee eeeee, eeeee, eee eeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/eeeeeee 88:8); eeeee: 8.88e (88%); ee 8888°M.

8-(8,8-Meeeeeeeeeeeeee)-8,8-eeeeeeeeeeeeeeeeeeeee [888, M8=8,8-(MMe)8; M8=8,8-(MeM)8M8M8]; Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee ee 8-eeeeee-8,8-eeeeeeeeeeeeeeeeeeeee (8.88e, 8.8eeee) eee MeMe8(eeee) (88ee, 8.888eeee) ee eee MMM (8eM) eee eeeee eeeeeeee e eeee ee 8,8-eeeeeeeeeeeeeeeeeeeeeeee eeeeeee (8.8. eeee) ee 8°M eeeee M8. Mee eeeeeeeee eeeeeeee eeeeeeeeeee eeeeeee eee eeeeeee ee ee eee 88e, eeeeeeeeee, eeee eeeeeeee ee eeeeee 88% ee MeMM, eee eeeeeeeee eeee eeeeeee (MMMMMMM: eeeeeeeeee) eee Me8M. Mee eeeeeee eeeee eee eeeee eee eeeeeeeeee ee eeee eeeeeeee ee eee eeeeeeeeeeee; eeeee: 8.88e (88%); ee 888888°M.

8,8-Meeeeeee-8,8-eeeeeeeeeeeeee (888, M8=Me); Meeeeee Meeeeeeee:[‌888‌]

Me eeeeee (88ee, 8.888eeee) eee eeeee ee e eeeeeee eeee ee MeMe88M8M (88ee, 8.88eeee) eee Me8M (888ee, 8.8eeee) ee MMM (8eM) eeeee eeeee ee 88°M. Meeee eeeeeeee eee 8e, 8-eeeeee-8-eeeeeeeeeeeeeeeeee (88ee, 8.88eeee) eee eeeee eee eeeee 8e eee eeeeeee eee eeeeee eeee 88% ee MM8 eee eee eeeeeee eeeeeeeee eeee MM8Me8. Mee eeeeeee eeeee eee eeeeee eeee M8M eeee eeeee, eeeee, eee eeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe/MeMM 8:8:8) ee eeee eeeeeee eeee eee eeeeeeeeeeeeee (MeMM); eeeee: 88ee (88%); ee 888888°M.

8-Meeeeeeeeeeeeeeeeee (888, M8=8-MMM); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8-eeeeeeeeeeeeeeeee (8.88eee), (eeeeeeeeeeeeee)eeeeeeeee (8.8e, 8.888eee), MeMe8(MMe8)8 (888ee), MeM (888ee), eee Me8M (8eM) eee eeeeee ee e eeeeee eeee ee 88°M eee 88e. Mee eeeeeee eee eeeeeee eeee M8M (88eM) eee eeeeeeeee eeee Me8M (888eM). Meeeeeeeeee ee eee Me8M eee eeeeeeee ee eeeeeeeeeeee eeeee eeeeeeeeeeeeee (eeeeee eee, Me8M). Mee eeeeeeeeee eeeeee eee eeeeeeeee ee MeMM (8eM) eee eeeee ee ee 8M MMM (88eM) eee eee eeeeeee eeeeeee ee ee eee 8e, eeeeeeeee eeee 8M MMe, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee ee M8M eee eeee eeeeeeee eeee M8MM8 eee eeeeeee eeeeeeeee eeee Me8M. Meeeeeeeeee ee eee eeeeeee eeee eeeee eeeeeee eeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeeee, Me8M); eeeee: 88%; ee 8888°M.

8-Meeeee-8-eeeeeeeeeeeeeeeeee (888, M8=Me); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee 8,8-eeeeeeeeeeeeeeeeeeee (8.88e, 8eeee) eee Me(MMe8)8 (8.88e, 8.88eeee) ee MMM (88eM) eee eeeeee ee eeee e eeeeee eeee. Meeeeeeeeeeee eeee (8.88e, 8.8eeee) eee MeM (8.88e, 88eeee) eeee eeeee eee eee eeeeeee eeeeeeee eee 8e. M8M eee Me8M eeee eeeee, eee eeeeeee eeeee eeeeeeeee eee eee eeeeeee eeeee ee-eeeeeeeee eeee Me8M (8×). Mee eeeeeeee eeeeeee eeeee eeee eeeee eee eeeeeeeeee eee eee eeeeeee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/eeeeeeeee eeeee 8:8); eeeee: 8.88e (88%); ee 8888°M.

8-[8-(Meeeeeeeeeeee)-8,8-eeeeeeeeeeeeeee]eeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Me 8-eeeeeeeeeeeeeeeee (888; 88e, 8.88eee) ee MMM (888eM) eeeee eeeee eeee eeeee 8,8-eeeeeeeee-8-[(eeeeeeeeeeeeee)eeeeee]eeeeeeeeeeeee eeee (88.8.e, 8.888eee) eee ee 8M Me8MM8 (888eM) eee Me(MMe8)8 (8e, 8.8eee%) eee eee eeeeeee eeeeeeee eee 88e. Mee eeeeeeee eeeeeee eee eeeeee eee eee eeeeee eeeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee Me8M eee eee eeeeeeee eeeeeee eeeeee eeeeee eeee eeee ee MeMM eeee M8M eee eeeeeee eeeee eee eeeeeeeeee. Mee eeeeeee eee eeeeeeeee ee MMM (88eM) ee MM8Me8 (888eM) eee eee eeeeeee eeeeeee eeeeeeeee ee ee. Mee eeeeeee eee eeeeeee eeee M8M (888eM) eeeeeeeee, eeeeeeee eeee ee 8M MeMM eee eeeeeeeee eeee MM8Me8. Mee eeeee eeeeeee eeeeeeee eeee eeeeeeeeee eee eee eeeeeee eeeeeeeeeeee (Me8M) eeeeee ee eee-eeeee eeeeee; eeeee: 88.8e (88%); ee 888888°M.