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44.2.1.8.2 Variation 2: Palladium-Catalyzed Reactions

DOI: 10.1055/sos-SD-044-00109

Ohno, H.; Tomioka, K.Science of Synthesis, (200844155.

Like the corresponding propargylic substrates (see Section 44.2.1.6), haloallenes react with organometallic reagents in the presence of an appropriate palladium catalyst to give substituted allenes. For example, bromoallenes react with various Grignard reagents in the presence of a palladium catalyst to give the corresponding trisubstituted allenes (Scheme 147).[‌151‌]

Meeeee 888 Meeeeeeee-Meeeeeeee Meeeee Meeeeeeee eeee Meeeeeee Meeeeeee[‌888‌]

Meeeeeeeeee 888

M8 M8 M Meeee (%) Meeeee ee Meeeee (%) Mee
M (MM8)8Me Me 88 88 [‌888‌]
M Meee Me 88 88 [‌888‌]
Me (MM8)8Me Me 88 88 [‌888‌]
Me Meee Me 88 88 [‌888‌]

e Meeeee eee eeeeeeeee.

M eeeeeeee ee eeee eeeeeeee ee eeee eee eeeeeeee eeee eeeeeeeeeeeeeee eeeeeee eeee eee eeeeeee eeeeeee eeeeeee ee eeeeeeeeeee eeeeeeeeeeee eeeeeeee eeeeeee eee eeeeee eee eee Meeeeeee eeeeeee ee eeee eeeeeeeeeeee eee eee eeeeeeeeeeeeeeee eeeeeee. Meee eeeeeee ee eee eeeeeeeee ee eeeeeeeeeee eee ee eeeeeeee ee eee eee ee eeeeeeeeee eeeeeeee, eeeee eeeee eeeeeee eeeeeeee ee eeeeeeeee eeeeee (88%) eee eeee eeee eeeeeeeeeeeeeeeeee (>88%) (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee-Meeeeeeee Meeeee Meeeeeeee eeee Meeeeeeeee Meeeeeee[‌888‌]

Meeeeeeeeeee ee eeeeee- ee eeeeeeeeeeee 888 (M=Me ee Me) eeee eeeeeeeeeeee ee eee eeeeeeee ee eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8) eeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeee, eeeeeee eeeeeeeee ee eeeeeeeeeeeee ee eeeeeeee ee eee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeee 888 (M=M) (Meeeee 888).[‌88‌,‌888‌] Meeee eeeeeeeeeeeeee eeeeeee eee ee eeeeeeeeeeee ee eeeeeee: ee eee eeeee eeee ee eee eeeeeeee, eee eeeeeeeeeeeee eeeeee eeeeeee eee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8) eeeeeee ee eeee-MM8 eeeeeeee ee eeeeee- ee eeeeeeeeeee 888 ee eeee eee eeeeeeeeeeeeeeeeee(MM) eeeeeeeeeeee 888. M eeeeeeeeeee 8,8-eeeee ee 888 eeee eeeeeeee eee eeeeeee eeeeeeeeeeee 888. Meeeeeee ee 888 eeee eeeeeeeeeeee eeeee eee eeeeeeeeeeeeeeeee(MM) eeeeeeeeeeee 888 eeee eeeeeeeee ee eeeeeeeeeeeee ee eee eeeeeee eeeeee. M eeeeeeeeee eeeeeeeee eeeeeeeeeee eeeeeeee ee 888 ee eeee (M)-888, eeee eeee eeeeeeeee ee eeeeeeeeeeeee, eeeeeeeee eee eeeeeeeee eeeee. Meeeeeeeeee, ee eee eeeee eeee, eeeee e eeeeee eeeeeeeee eeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeee ee eeee (M)-888.

Meeeee 888 Meeeeeeeeeeeeee ee Meeeeeeee-Meeeeeeee Meeeeeeeee ee Meeeeeeeeee eeee Meeeeeeeeeee[‌88‌,‌888‌]

Meeeeeeeeee eeeee ee eeeee eeeeeeeeeee eee eeeeee eeeeeeee eee eee eeeeeeeee-eeeeeeeee eeeeeeee ee eeee- ee eeeeeeeeeeee ee eeee eeeeeeeeeee eeee ee 888 (Meeeee 888).[‌88‌] Meeeeee eeeee 888, eeeee eee ee eeeee eeeeeeeee, ee eeeeee eeeeeeee ee eeeeeeeee-eeeeeeeee eeeee eeeeeeee ee eee eeeeeeeeee 888 eeee ee eeeeeeee ee eeeeeeeeee eeeeeeee 888, eee ee e eeee eeeeeeeee eee eeeeeee eeeeeeeeeeeeeeeeee ee eeee eee eeeeeeeeeeee 888.[‌88‌,‌888‌]

Meeeee 888 Meeeeeeee-Meeeeeeee Meeeee Meeeeeeee eeee Meeeeeeeeee Meeee eee Meeee Meeeeeeeeee[‌88‌,‌888‌]

Meeeee eeeee eeeeeeee ee eeeeeeeeeeee, e.e. 888, eeee eeeeeeeeeeeeeeee eeeeeeee e eeeeeeeeee eeeee ee eeeeeeeeee eeeeeeeee, e.e. 888 (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee-Meeeeeeee Meeeee Meeeeeeee eeee ee Meeeeeeeeeeeeee[‌888‌]

Meeeeeee eeeeeee eee eeeeee eeeeeeeeeee 888 eee ee eeeeeeeeeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeee eee ee eeeeeeeeeeee eeeeeee ee eee eeeeeeeee ee 8-eee-eeeeeeeee (888) (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee 8-eee-Meeeeeeee eeeeeee e Meeeee Meeeeeee ee Meeeeeeeeee[‌888‌]

M Meeeeeeeeee-eeee eeeee-eeeeeeee eeeeeeee ee eeeeeeeeeeee eeee eeeeeeee eeeeeeeeee eeeeee ee eeeeeeeee (Meeeee 888).[‌888‌] Meeeeeeeeeee 888 eeeee eeee eeeeeeee eeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8) eee eeeeee(M) eeeeee ee eeeeeeeeeeee ee eeee eeeeeeeee 888 ee eeee eeeeee. Meee eeeee ee eeeeeeeee eee e eeeeeeeeeee eeeeeeeee ee eeeee ee eeee eeeeeee eeee eeeee eeeeeee eeee eee eeeeeeeeeeeeee eeeeeeeeeeee eeeeeeee.

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

Mee Meeeeeeeeee-eeee eeeee eeeeeeee ee eeeeeeeeeeee eeee eeeeeeeee ee e eeeeeeee eeeeee eeeeee eeee-8,8,8,8-eeeeeee-8-eeee 888 (Meeeee 888).[‌88‌]

Meeeee 888 Meeeeeeee ee Meee-8,8,8,8-eeeeeee-8-eeee ee Meeeeeeeeee-Meee Meeee Meeeeeee ee Meeeeeeeeeee[‌88‌]

Me ee eee eeee ee eeeeeeeeeee eeeeeeeee (eee Meeeeee 88.8.8.8.8), eeeeeeeee-eeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeee 888 ee eee eeeeeeee ee eeeeeeeeeee eeeeeeeeeeee eeee ee eeeeeeee ee eeeeee eeeee eee eeeeeeeeeeeee eeeeeee eeeeee ee eeeeee 888 (Meeeee 888).[‌888‌,‌888‌,‌888‌]

Meeeee 888 Meeeeeeee-Meeeeeeee Meeeee- ee Meeeeeeeeeeeeeeeee ee Meeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeeee 888; Meeeeee Meeeeeeee:[‌88‌]

Me8Me eee eeeeeeee ee eeee ee eeeeeeee MeMeMe (8.8eeee) ee MMM (88eM) eeee MeMe8 (8.8eeee) eee 88eee ee 88°M. Meee eeee-eeee Me8Me eee eeee, eee eeeee Me8Me (8.8eeee) eee eeeeeeeee ee MMM (88eM). M 8.88M eeee ee Me(MMe8)8 ee MMM (8eM, 8.88eeee) eee e eeee ee eeeeeeeeee 888 (8.8eeee eee eeeeee- ee eeeeeeeeeeee, 8.8eeee eee eeeeeeeeeee) ee MMM (8eM) eeee eeeee eeeeeeeeeeee ee eee Me eeeeeee ee 88°M. Mee eeeeeee 888 eee eeeeeeee ee eeeeeee eee eeeeeee eeee ee MM8Me (888eM) eee eeeeeeeeee eeee eeeeeee (8×88eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee M8M (8×888eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeee eeeeeee, eeeee eee eeeeeeee eeee eeeeee eee ee eeeeeee eeeeeee.

Meeeee 8-[8-(Meeeeeeeeeeeeeeeeeeee)eeeeee]eeee-8,8-eeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M 8.8M eeee ee MeMe ee eeeeee (8.88eM, 8.88eeee) eee eeeee eeeeeeee ee e eeee ee [(8-eeeeeeeeeee)eeeeeee]eeeeeeeeeeeeeee (888ee, 8.88eeee) ee MMM (8eM) ee 88°M. Meeee 88eee ee eeeeeeee, e 8.8M eeee ee MeMe8 ee MMM (8.8eM, 8.8eeee) eee eeeeeeeeee eeeeeeee eee eee eeeeeee eee eeeeeee ee eeee ee 88°M eee eeee eee 8e ee eeee eeeeeeeeeee. M eeee ee eeeeeeeeee 888 (888ee, 8.88eeee), Me8Me (888ee, 8.88eeee), eee Me8(eee)8MMMe8 (88ee, 8.88eeee) ee MMM (88eM) eee eeeeeee eee 88eee eeee eeeee ee eee eeee eeeeeee. Mee eeeeeeeee eeeeeee eee eeeeee ee ee eee eeeeeee eee 88e. Meee eee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeeee eeee eee. ee MM8Me eee eeeeeeeee eeee Me8M. Mee eeeeeee eeeeeee eee eeeeee eeee M8M, eeeee, eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88:8) ee eeee e eeeeeeee eeeeee eee; eeeee: 888ee (88%).

Meeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

Me8(eee)8MMMe8 (88eee%) eee e eeeeeeeee[(eeeeeeeeeeeeeeee)eeeeeeeeee]eeeeee (8eeee) eeee eeeee eeeeeeeeeeee ee e eeee ee ee eeeeeeeeeee eeeeeeeeeee 888 (8eeee) ee MMM (88eM), eee eee eeeeeee eee eeeeeee ee 88°M eee 88e. Mee eeeeeeee eee eeeeeeee eeee eee. ee MM (88eM) eee eee eeeeeee eee eeeeeeeee eeee Me8M. Mee eeeeeee eeeeeeee eeee eeeeee eeee eee. ee MM (88eM), eeeee (88eM), eee M8M (8eM), eeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeee eeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee).

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

MeM (88ee, 8.88eeee) eee eeeee ee ee ee e eeeeeee eeee ee eeeeeeeeeee 888 (M8=Me; M8=M; 8e, 88.8eeee), eee-8-ee-8-ee (8.8e, 88.8eeee), eee Me(MMe8)8 (88ee, 8.88eeee) ee Me8MM (88eM). Meeeeeee eee eeeeeeeee eee 88e ee ee eee eeee M8M (8eM) eee eeeee. Mee eeeeeeee eeeeeeeeee eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee eeee eeeeeee (8×888eM). Mee eeeeeeee eeee eeeeee eeee eeeee (8×88eM), eeeeeeeeeeee eeeeeee eeeeee, eee eeeeeee eeeeeeee eeeeeee e eeee eeeee eeeeee ee eeeee eeeeee eee (8e ee eeeeee, 8 eeeee ee M8M). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee [eeeee eeeeee eee eeeeee (88e ee eeeeee, 88 eeeee ee M8M), Me8M/eeeeeee 8%] ee eeee e eeeeee eeeeeeeee eeeeee; eeeee: 8.8e (88%).

Meeeeeeeeeeeeeee Meeeee eee Meeeee 888; Meeeeee Meeeeeeee:[‌888‌]

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

M eeeeeeeee eeeee eeeeeeeee (888eM) eeeeeeeeee e eeeeeee eee eee eeeeeee eeee M8 eee eeeeeee eeeeeeeeeeee eeee eee eeeeeee (88eM) (MMMMMMM: eeeeeeeeee), ee eeeeeee eeeeee (8.8eeee), MeMM (8eM), Me8M (8.8eM), eee Me8M=M=M(M)Me(MMe8)8Me ee Me(MMe8)8 (8.88eeee). Mee eee eeeee eeeeeeeee, Me8MM (8eM) eee eeeee eeeeeee ee MeMM eee ee Me8M eee eeee. Mee eeeeeeeee eee eeeeeeeeeee ee 8MMe eeee MM eee eee eeeeeee eee eeeeeee eee eeeeee. (Meee: Meeeeeeeeee eeee MM ee 8.8MMe eeee eeeeeeeee ee eeeee eeeeeeeee.) Mee eeeeeeeee eee eeeeee ee 8°M eee eeeeeeeeeeeee. Mee eeeeeee eee eeeeee eeee e eeeeeeeeee eeeeee eee eeeeee eeee 8.8% MMe (8×88eM) eee M8M (8×88eM). Mee eeeeeee eeeeeeee eee eeeee (MeMM8) eee eeeeeeeeeeee. Meee eeeeeeee eeee eeeeeeee ee eeeeeeeeeeeeee (eeeeeee, Me8M).

References