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1.1.1.1.1.1.2.5 Vinyl 4-Toluenesulfonate Electrophiles

DOI: 10.1055/sos-SD-207-00004

Guram, A. S.; Milne, J. E.; Tedrow, J. S.; Walker, S. D.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2013173.

Similarly to the enol trifluoromethanesulfonates, the scope of cross coupling with 4-toluenesulfonate electrophiles is significantly expanded in the enol 4-toluenesulfonate regime. More reactive than their aryl congeners, enol 4-toluenesulfonates can be coupled with arylboronic acids under milder conditions. Activated enol 4-toluenesulfonates (those bearing a conjugated electron-withdrawing group) may be coupled with simple arylphosphine-based ligands under palladium catalysis.

Me eeeeeee ee eee eeee eeeeeeeeeeeeeeeeeeeeeeeee eeeee-eeeeeeee eeeeeeeee ee eee eeeeeeeeee eeeeeee (eee Meeee 88), eeee 8-eeeeeeeeeeeeeeee 88 eeeeeeeee eeeee-eeeeeeee eeeeeeee eeee eeeeeeeeeeeee eeee eeeee [8,8′-eee(eeeeeeeeeeeeeeeee)eeeeeeeee]eeeeeeeeeeeeeeeee(MM) [MeMe8(eeee)] ee e eeeeeeee eeee eeeeeeeee eeeeeeeee ee 88 °M (Meeeee 88).[‌888‌] Mee eeeeeee ee eeeeeeee eeeeee eeeee eeeee eeeeeeeeee eee eeeeeeee eeeeeeeeeeee, eee eeeee e 88% eeeeeeee eeeee ee 88 eee ee eeeeeeee.

Meeeee 88 Meeeeeeee ee e Meeeee Meeeeeeeee Meeeeeeeee Meeee Meee 8-Meeeeeeeeeeeeeee Meeee Meeeeeee eeee Meeeeeeeeeeee Meee[‌888‌]

Meeeee eee eeeeeee ee γ-eeeeeeeeeeee eeee eeeeeeeee, ee eee eeee eeeee eeee eeeeeeeeeeeeeeeee eeeeeee eeeeeee eeee 8-eeeeeeeeeeeeeeeee 88 eeeeeee eeee β-eeee eeeeee eeeeeee Meeeee–Meeeeee eeeeeeee eeee eeeeeeeeeee eeeee ee eeeeeeeeeeeee 888 eeeee eeee eeee eeeeeeeeee eeee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) ee eeeeeeee.[‌888‌] Meeeeeeeee eee eeeeeeeee eeeeeeeee ee eeee M- eee M-eeee 8-eeeeeeeeeeeeeeeee eee eeeeeeee, eee eeee eeeeee eeeeeee eeeeeee eeeee eeeeeeee eeeee eee eeeeeeee eeeeeeeeee, eeeeeeee eee M-eeee 8-eeeeeeeeeeeeeeeee eeeeee eeeeeeeeee eeeee eeeeee. Meee eeee 8% eeeeee eeeeeeeeeeeee ee eeeeeeee eeeee eee eeeee-eeeeeeee eeeeeeeeee, eeeee eeeeeeee eeeeeee ee eeeeeeee/eeeeeeeeeee eeeeeee eee eeeeeeee. Meee eee eeee-eeeeeeeeeeeeee eee eeeeeeeeeeeeeeeee eeeeeeeeee eeeeee eee eeeeeeeee ee eeeeeeee, eee eeeeeeee-eeeeeeee eee eeeeeeee-eeeeeeeeeee eeeeee ee eee eeeeeee eeee eee eeee eeeeeeeeee (Meeee 88, eeeeeee 8–8).

Meeeeeeee eeee 8-eeeeeeeeeeeeeeeee 88 eeeeeee eeee eeeeee eeeeeee eeee ee eeeeeeeeeeee,[‌888‌] eeeeeeeee,[‌888‌,‌888‌] eeeeeeeee, eee eeeeeeeee[‌888‌] eeeeeee eeeee eeeeeeee eeee eeeeeeeeeee eeeee eeeee e eeeeeee ee eeeeeeeeee. 8-[8-(Meeeeeeeeeeeeeeeeeeee)eeeeee]-8-eeeeee-8M-eeeeee (MM-Meee) eeeee eeeee eeeeeeeee eeeee eeee eeeeeee ee eee eeeeeeeee ee eee eeee 8-eeeeeeeeeeeeeeee eee eeeeeee eeee eee eeeee eeeeeeee.[‌888‌] Mee eeeeeeee ee eeeeeeeee eeee 8–8 eee% eeeeeeeee eeeeeeee eeee e eeeee-ee-eeeeee eeeee ee 8:8. Meeeeeeee eeeeeeeee ee eeee-eeeee eeeeeee ee 88 °M ee eeeeeeeeee ee eeeeeee eeee ee eeeeeeeee eeeeee ee eee eeee-eeeeeeeeeee eeeeeeeeeeee 888. Meeeeeee-eeee eee eeeeeeee-eeee eeeeeee eeeee ee eeee ee eeeeeeeeee eeeeeeeee 8,8-eeeeeeeeeeeeeeeeeeeee eeeee eee eeeeeeeee (Meeee 88).

Meeee 88 Meeeee–Meeeeee Meeeeeeee ee Meeeeeeee Meee 8-Meeeeeeeeeeeeeeee eeee Meeeeeeeeee Meeee[‌888‌,‌888‌]

Meeee M8 Me8 Me8M(MM)8 (Meeee) Meeeeeeeee Meeee (%) Mee
8 8-MM8M8 8.8 MeMe8(MMe8)8 (8 eee%), 8 M Me8MM8 (8.8 eeeee), MMM, 88 °M 88 [‌888‌]
8 8-Mee 8.8 MeMe8(MMe8)8 (8 eee%), 8 M Me8MM8 (8.8 eeeee), MMM, 88 °M 88 [‌888‌]
8 8-(MMM)M8M8 8.8 MeMe8(MMe8)8 (8 eee%), 8 M Me8MM8 (8.8 eeeee), MMM, 88 °M 88 [‌888‌]
8 8-MeMM8M8 8.8 MeMe8(MMe8)8 (8 eee%), 8 M Me8MM8 (8.8 eeeee), MMM, 88 °M 88 [‌888‌]
8 8-MeM8MM8M8 8.8 MeMe8(MMe8)8 (8 eee%), 8 M Me8MM8 (8.8 eeeee), MMM, 88 °M 88 [‌888‌]
8 8-MeMM8M8 8.8 MeMe8(MMe8)8 (8 eee%), 8 M Me8MM8 (8.8 eeeee), MMM, 88 °M 88 [‌888‌]
8 Me 8 Me(MMe)8 (8–8 eee%), MM-Meee (8–8 eee%), M8MM8M8M (8 eeeee), e-MeMM, 88 °M 88 [‌888‌]
8 Me 8 Me(MMe)8 (8–8 eee%), MM-Meee (8–8 eee%), M8MM8M8M (8 eeeee), e-MeMM, 88 °M 88 [‌888‌]
8 Me 8 Me(MMe)8 (8–8 eee%), MM-Meee (8–8 eee%), M8MM8M8M (8 eeeee), e-MeMM, 88 °M 88 [‌888‌]
88 Me 8 Me(MMe)8 (8–8 eee%), MM-Meee (8–8 eee%), M8MM8M8M (8 eeeee), e-MeMM, 88 °M 88 [‌888‌]
88 8-MeM8M8 8 Me(MMe)8 (8–8 eee%), MM-Meee (8–8 eee%), M8MM8M8M (8 eeeee), e-MeMM, 88 °M 88 [‌888‌]
88 8,8-Me8M8M8 8 Me(MMe)8 (8–8 eee%), MM-Meee (8–8 eee%), M8MM8M8M (8 eeeee), e-MeMM, 88 °M 88 [‌888‌]
88 8-MeM8MM8M8 8 Me(MMe)8 (8–8 eee%), MM-Meee (8–8 eee%), M8MM8M8M (8 eeeee), e-MeMM, 88 °M 88 [‌888‌]

Meeeeeeeeee eeee 8-eeeeeeeeeeeeeeeee eee eeee ee eeeeeeeeeeee eeeeeee eee e eeeeeee ee eeeeeeeee eeeeeee. Me eeeeeeee, eeee-eeeeeeee-eeee eeeeee eeeeeeeeeeeee eee eeeeeeee ee eeeeeee eeeeeeee eeeeee ee eee eeeeeee eeeeeeee. Meeee eee eeeeeeeee eeeeeeeee eeee eeee 8-eeeeeeeeeeeeeeeee eeee eeee eeeee eeeeeeeeeeeeeeeeeeeeeeeee eeeeeeeeeeee, eeeeee eeeeeeeeeeeee eeeee 8-eeeeeeeeeeeeeeeee ee eeeeeeeeeee eeeee 8-eeeeeeeeeeeeeeeee eee ee eeeeeeee ee eeeeeeee e eeeeeee ee eeeeeee eee eeeeeeeeeee eeeeeee eeeeeeeeeee. Me eee eeee eeeee eeee eeeeee eeeee 8-eeeeeeeeeeeeeeee eee ee eeeeeee eeee e eeeee ee eeeeeeeeeee eeeee ee eeeeeeee eee eeeeeeeeeee eeeeeee eeeeeeeeeee.[‌888‌] Meee 8 eee% ee eeeeeeee eeeeeeeee MM-MM88-M (888) (Meeeee 88) eee eeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeee/eeeee, eeeeee ee eee eeeeeeeeeeeee eeeeeeee 888 (M8 = M8 = M8 = M) eeeee eeee eeeeeeee ee eeeeeeeee, eee e eeee eeeeeee ee eeeeeeeeee eeeeee ee eee eeeeeee eeee eeeeeee ee eeeeeeeee (Meeee 88, eeeeeee 8–8). Meeeeeeee, eeeeeeeeeeeeeeee 888 (M8 = M8 = M; M8 = M) eee ee eeeeeeee eeee 8,8-eeeeeeeeeeeee 8-eeeeeeeeeeeeeeee eeee eeee ee eeeeeeee eeeeee eee eeeeeee eeeee eeee eeeeeee ee eee eeeeeee eeeee (Meeee 88, eeeeeee 8–8). Mee eee eeeeeeeeeeeeeeee, eeeeeee, eee eeeeeeeee eeeeeeee eeeeee ee eeee(eeeeeeeeeeeeeeeeeeee)eeeeeeeeeee(8) (8.8 eee%) eee eeeeeeeeeeeeeeeeeeeeee (8 eee%) ee eee eeeeee. (M)-8-Meeeeeeeeee 8-eeeeeeeeeeeeeeee ee e eeeeeeeee eeeeeeee eeeeeee ee eeeeeeee eeeeeeeeeeeeeeeee eeeeeeeeeee 888 (M8 = M8 = M; M8 = M) (Meeee 88, eeeeeee 8–8).[‌888‌]

Meeeee 88 Meeeeee Meeeeee eee Meeeeeeeeeee Meee ee Meeeeeeee-Meeeeeeee Meeee Meeeeeeee ee Meeeeeeeeee Meee 8-Meeeeeeeeeeeeeeee eeee Meeeeeeeeee Meeee

Me eeeeeeee ee eeee 8-eeeeeeeeeeeeeeeee, 8-(eeeeeeeeeeeeeeeeeeeee)-8′,8′,8′-eeeeeeeeeeeeeeeeeeee (MMeee) eee ee eeee eeee e eeeeeee eeeeee ee eeeeeeeeeee eeee 8-eeeeeeeeeeeeeeeee.[‌888‌] Mee eeeeeee eeeee eeee ee eeee eeeee eee eee eeee eeeeeeeeeee eeeeeeee-eeee eeeeeeeeeeee, eee eeeee eee eeeeeeee eeeeeeeeee eeeeeeee eee eeee 8-eeeeeeeeeeeeeeeee, eeeeeeeee eeeeee eee eeeeeeee ee eeee eeeee (Meeee 88, eeeeeee 88 eee 88). Meeeeeeee, 8-[8-(eeeeeeeeeeeeeeeeeeeee)eeeeee]-8-eeeeee-8M-eeeeee (MM-Meee) ee eeeeeeeee ee eeeee eeeeeeee ee e eeeeeee ee eeeeeeeeeee eeee 8-eeeeeeeeeeeeeeeee.[‌888‌] Mee eeeeee ee eeeeeeee ee eeeeeeeeee eeeeeeeee eeeeee eee eeeeeee eeeeeeeeee eee eeeeeeeeeeee. Mee eeeeeee eeeee eeeeeee eeee eee eeeee ee eeeeeeee-eeeeeeeeeee eee eeeeeeee-eeeeeeee, eee eeeeee eee eeeeeee eeeeeeeeeee 888 ee eeeeeeee ee eeeeeeeee eeeeee (Meeee 88, eeeeeee 88–88).

Meeee 88 Meeeee–Meeeeee Meeeeeeee ee Meeeeeeeeee Meee 8-Meeeeeeeeeeeeeeee eeee Meeeeeeeeee Meeee[‌888‌,‌888‌‌888‌]

Meeee M8 M8 M8 Me8 Meeeeeeeee Meeee (%) Mee
8 M M M 8-MMM8M8 888 (8 eee%), M8MM8 (8.8 eeeee), eeeeeee/M8M, 888 °M 88e [‌888‌]
8 M M M 8-MeMMM8M8 888 (8 eee%), M8MM8 (8.8 eeeee), eeeeeee/M8M, 888 °M 88e [‌888‌]
8 M M M 8-(MMM)M8M8 888 (8 eee%), M8MM8 (8.8 eeeee), eeeeeee/M8M, 888 °M 88e [‌888‌]
8 M M M Mee Me8(eee)8MMMe8 (8.8 eee%), Me8M (8 eee%), M8MM8 (8.8 eeeee), eeeeeee, 888 °M 88e [‌888‌]
8 M M M 8-MMM8M8 Me8(eee)8MMMe8 (8.8 eee%), Me8M (8 eee%), M8MM8 (8.8 eeeee), eeeeeee, 888 °M 88e [‌888‌]
8 M M M 8-M8MM8M8 Me8(eee)8MMMe8 (8.8 eee%), Me8M (8 eee%), M8MM8 (8.8 eeeee), eeeeeee, 888 °M 88e [‌888‌]
8 M M M 8-MMM8M8 Me8(eee)8 (8.8 eee%), Me8MMMM8 (8 eee%), M8MM8 (8.8 eeeee), eeeeeee/M8M, 888 °M 88e [‌888‌]
8 M M M 8-MeMMM8M8 Me8(eee)8 (8.8 eee%), Me8MMMM8 (8 eee%), M8MM8 (8.8 eeeee), eeeeeee/M8M, 888 °M 88e [‌888‌]
8 M M M 8-MeM8M8 Me8(eee)8 (8.8 eee%), Me8MMMM8 (8 eee%), M8MM8 (8.8 eeeee), eeeeeee/M8M, 888 °M 88e [‌888‌]
88 M (MM8)8 8-Me8MMMM8M8 Me(MMe)8 (8–8 eee%), MMeee (8–8 eee%), M8MM8M8M (8 eeeee), MMM, 88 °M 88e [‌888‌]
88 M MM8MM(e-Me)(MM8)8 8-MMM8M8 Me(MMe)8 (8–8 eee%), MMeee (8–8 eee%), M8MM8M8M (8 eeeee), MMM, 88 °M 88e [‌888‌]
88 Me Me Me Me Me(MMe)8 (8–8 eee%), MM-Meee (8–8 eee%), M8MM8M8M (8 eeeee), e-MeMM, 88 °M 88e [‌888‌]
88 M MMe8MMMMe8MM8 8-Mee Me(MMe)8 (8–8 eee%), MM-Meee (8–8 eee%), M8MM8M8M (8 eeeee), e-MeMM, 88 °M 88 [‌888‌]
88 Me 8-MeMM8M8 Me(MMe)8 (8–8 eee%), MM-Meee (8–8 eee%), M8MM8M8M (8 eeeee), e-MeMM, 88 °M 88e [‌888‌]
88 Me 8-MeM8MM8M8 Me(MMe)8 (8–8 eee%), MM-Meee (8–8 eee%), M8MM8M8M (8 eeeee), e-MeMM, 88 °M 88 [‌888‌]

e 8.8 eeeee ee eeeee 8-eeeeeeeeeeeeeeee eee eeee eee eeeeeee eeee.

e 8.8 eeeee ee eeeeeee eeee eee eeee.

e 8 eeeee ee eeeeeee eeee eee eeee.

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeeee (Meeee 88, Meeeeee 8–8); Meeeeee Meeeeeeee:[‌888‌]

M Meeeeee eeeee eee eeeeeee eeee eee eeee 8-eeeeeeeeeeeeeeee 88 (8.8 e, 8.88 eeee), eee eeeeeeeeeee eeee (8.88 eeee, 8.8 eeeee), eee MeMe8(MMe8)8 (8 eee%, 8.88 eeee). MMM (8 eM) eee eeeee eeeeeeee ee 8 M Me8MM8 (8.8 eM, 8.88 eeee), eee eee eeeee eee eeeeeeeee eee eeeeeeeeee eeee M8 (8 ×). Mee eeeeeeeee eeeeeee eee eeeeeee eeeeeeeee ee 88 °M eeeee M8. MMMM eeeeeeee ee eee eeeeeee eeeeeeeee eeeeeeee eeeeeeeeee. Mee eeeeeee eee eeeeee ee ee eee eMeMMe (88 eM) eee eeeee eeeeeeee ee MeMMM8 (8 eM) eee M8M (8 eM). Meeee eee eeeee eee, eee eeeeeee eeeee eee eeeeeeeee eeee eMeMMe (8 × 88 eM). Mee eeeeeee eeeeee eeee eeeeee eeee 8.8 M MeMM (8 × 88 eM) eee eeeee (8 × 88 eM). Mee eeeeeee eeeee eee eeeee (MeMM8) eee eeeeeee eeee MM-M Meeee (88 ee), eee eeeeeeee eeeeeee Meeee Meee. Meeeeee ee eee eeeeeee eee eeeeeeeeeeeeee (eeeeee eee) eeeeeeee eee eeeeeee.

Meeeeeee (Meeee 88, Meeeeee 8–8); Meeeeee Meeeeeeee Meeee Meeee 8-Meeeeeeeeeeeeeee:[‌888‌]

Mee eeeeeee eeee (8.8 eeeee), eeeee 8-eeeeeeeeeeeeeeee (8.8 eeeee), eee MM-MM88-M (888; 8.88 eeeee) eeee eeeeeeeee ee eeeeeee (8 eM). Meee, 8 M M8MM8 (8.8 eM) eee eeeee, eee eee eeeeee eeee eee eeeeee eeee e Meeeee-eeeeee eeeee eee eee eeeeeee eeee eee eeeeeeee. Mee eeeeeee eee eeeeee eee 88–88 e ee 888 °M. Mee eeeeeeee eee eeeeeeeee ee MMM. Meeee eeeeeeeeee, eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee.

(8,8-Meeeeeeeeeeee)eeeeeeee (Meeee 88, Meeeeee 8–8); Meeeeee Meeeeeeee Meeee 8,8-Meeeeeeeeeeee 8-Meeeeeeeeeeeeeee:[‌888‌]

8,8-Meeeeeeeeeeee 8-eeeeeeeeeeeeeeee (e.8 eeeee), eeeeeee eeee (8.8 eeeee), Me8M•MMM8 (8.88 eeeee), eee Me8(eee)8 (8.88 eeeee) eeee eeeeeeeee ee eeeeeee (8 eM). Meee, 8.88 M M8MM8 (8.8 eM) eee eeeee, eee eee eeeeee eeee eee eeeeee eeee e Meeeee-eeeeee eeeee eee eee eeeeeee eeee eee eeeeeeee. Mee eeeeeee eee eeeeee eee 88 e ee 888 °M eee eeeeeeeee ee MMM. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeeee eeeeeee Meeeee eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee.

Meeeeeeeeeeee 888 (Meeee 88, Meeeeee 88–88); Meeeeee Meeeeeeee Meeee Mee-8-eeee 8-Meeeeeeeeeeeeeeee:[‌888‌]

Me(MMe)8 eee 8-[8-(eeeeeeeeeeeeeeeeeeeee)eeeeee]-8-eeeeee-8M-eeeeee (MM-Meee) (Me/Meeeee = 8:8) eeee eeeeee eeee e Meeeeee eeee eeeeeeee eeee e Meeeee-eeeeee eeeeeeee eeeeeee eee. Mee eeee eee eeeeeeeee eee eeeeeee eeee M8 eeeeeee eeeee. Meeeeeeeeeeeeee eee eeeeeeeeeeee ee eeeeee eeeeeee eeeeeeeee MM8Me8 (8 eM) eee Me8M (888 µM) eeee eee eeee. Mee eeee eee eeeeeee eee eeeeee eeeee e eeee eeeee eee eeeee 8–8 eee eeeee eee eeeeeee eeeeeee eeeeeee. Mee eeeeeee eee eeee eeeeeee eeeee eeee eeeeee. Mee eeeeeee 8-eeeeeeeeeeeeeeee (8.8 eeee), eee eeeeeeeeeee eeee (8.8 eeee), eee M8MM8•M8M (8.8 eeee) eeee eeeeee eeee eee eeee, eee eee eeeeee eee eeeeeee eeeeeeeee eee eeeeeee eeee M8 eeeeeee eeeee. e-MeMM (8.8 eM) eee eeee eeeee. Mee eeee eee eeeeeee ee ee eee eeeeeee eee eee eeee eeeeee eeee e eeeeeeeee eee eeee (88–888 °M) eee 88 e. Meeee eeeeeeeeee ee eee eeeeeeee ee eeeeee ee MM eeeeeeee, eee eeee eee eeeeeee ee eeee ee ee. Mee eeeeeeee eee eeeeeeee eeee M8M eee eee eeeeeee eee eeeeeee eeee MeMMe. Mee eeeeeee eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeee eeee MeMMe. Mee eeeeeee eee eeeeeee eeee eee eeeeeeee eeeeeee eeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee [eeeeee eee (888–888 eeee)].

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