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1.1.4.2.3.3.2 (Ammoniomethyl)- and (Aminomethyl)trifluoroborates

DOI: 10.1055/sos-SD-207-00131

Sandrock, D. L.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20131335.

(Ammoniomethyl)trifluoroborates have been prepared and shown to be suitable nucleophilic partners for the Suzuki–Miyaura cross-coupling reaction. Using palladium(II) acetate and XPhos, a variety of (ammoniomethyl)trifluoroborate substrates react with aryl and hetaryl chlorides to give benzylic amines 16 (Scheme 12).[‌29‌]

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Meeeeeeeeee 88

M8 M8 Me8 Meeee (%) Mee
(MM8)8 8-MMM8M8 88 [‌88‌]
(MM8)8 88 [‌88‌]
(MM8)8 88 [‌88‌]
Me Me 8-MeMM8M8 88 [‌88‌]
(MM8)8MMee(MM8)8 8-MeMM8M8 88 [‌88‌]
(MM8)8M(MM8)8 8-MeMM8M8 88 [‌88‌]

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

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Meeeeeeeeee 88

M8 Me8 Meeee (%) Mee
Me 88 [‌88‌]
Me 8-MMMM8M8 88 [‌88‌]
eeeeeeeeeee 8-MeMM8M8 88 [‌88‌]
e-Me 8-MeMM8M8 88 [‌88‌]
Me 8-eeeeeee 88 [‌88‌]
Me 88 [‌88‌]

Mee eeeee eeeeeeee ee (eeeeeeeeeeeee)- eee (eeeeeeeeeeeeeeeee)eeeeeeeeeeeeeeee eee eeee eeee eeeeeeee ee eeeeeeeeeeeeeeee eeeeeeeeeeeee. Meeee eeee eee eeee eeeee eee eeeeee ee eeeeee eeee eeeee eeeeeeeee-eeeeeeeeee eeeeeeeeeee, eeeeeeeeeeeeeeeee eee ee eeeeeeeeee eee eeee-eeeeeeeeee eeeeeeeeeee ee 8-eeeeeeeeeeeeeeeee. Meeee eeeeeeeee(MM) eeeeeee eee MMeee, eeee eeeeeeee eeeeeeee eeeeeeeeee eeeee ee eeeeeeeee eee eeeee eeeeeeee ee eeeeeeee (eeeeeeeeeee)eeeeee 88 eee (eeeeeeeeeeeeeeeee)eeeeee 88 (Meeeee 88).[‌88‌]

Meeeee 88 Meeee Meeeeeee ee (Meeeeeeeeee)- eee (Meeeeeeeeeeeeeeee)eeeeeeeeeeeeeeee eeee Meee eee Meeeeee Meeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Me8 Me(MMe)8 (eee%) MMeee (eee%) Meeee (%) Mee
(MM8)8 8-eeeeeeee 8 8 88 [‌88‌]
(MM8)8M(MM8)8 8-eeeeeeee 8 8 88 [‌88‌]
(MM8)8 8-MeMM8M8 8 88 88 [‌88‌]
(MM8)8 8-eeeeeee 8 8 88 [‌88‌]

Meeeeeeeeee 88M

M8 Me8 Me(MMe)8 (eee%) MMeee (eee%) Meeee (%) Mee
Me 8-eeeeeeee 8 8 88 [‌88‌]
e-Me 8-eeeeeeeeeee 8 8 88 [‌88‌]

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Meeeee 88 Meeee Meeeeeee ee eeee-Meeeeeeeeeeeee-Meeeeeeee Meeeeeeee (Meeeeeeeeee)eeeeeeeeeeeeeee eeee Meee eee Meeeeee Meeeeeeee[‌88‌]

Meeeeeeeeee 88

Me8 Meeee (%) Mee
8,8-Me8M8M8 88 [‌88‌]
88 [‌88‌]
8-M8MM8M8 88 [‌88‌]
8-eeeeeee 88 [‌88‌]
88 [‌88‌]
eeeee-8-ee 88 [‌88‌]

M-(Meeeeeeeee)eeeeeeeeeeee eee ee eeeeeeeee eeeee ee eeeeeeeee, eeeeeee eeeeee eeeeeeeeee eeeeeeee ee e eeeeeee ee eeeeeeeeeee eeeee. Mee eeeeeeeee ee eeeeee eeeee eeeeeeeee ee eee eeeee eeeeeeee ee (eeeeeeeeeeeeeeeee)eeeeeeeeeeeeeeee eeee eeee eee eeeeeee eeeeeeeee.[‌88‌] Meeee eee(eeeeeeeeeeee)eeeeeeeeeeeeeeeee(MM) eee MeMeee, eee eeeeeeeeeeeee eeeee-eeeeeee eeeeeeeeeeeeeeeee 88 eee eeeeeeee ee eeee ee eeeeeeeee eeeeee (Meeeee 88).

Meeeee 88 Meeee Meeeeeee ee (Meeeeeeeeeeeeeeee)eeeeeeeeeeeeeeee eeee Meee eee Meeeeee Meeeeeeee[‌88‌]

Meeeeeeeeee 88

Me8 Me8 Meeee (%) Mee
Mee 88 [‌88‌]
Mee 8-MeMM8M8 88 [‌88‌]
Mee 8-eeeeeee 88 [‌88‌]
8-MeMM8M8 8-MeMM8M8 88 [‌88‌]
8-eeeeeeee 8-MeMM8M8 88 [‌88‌]
8-MM8M8 8-MeMM8M8 88 [‌88‌]

Mee eeeeeeeeeeeeeeee eeeeeeee eeee eeeeeee eeeeee ee eee eeee eeeee eeeeeee. Mee eeeeeeeee ee eeeeeeeee (eeeeeeeeeeeeeeeee)eeeeeeeeeeeeeee (88) eee ee eeeeeeeeeeee eee e eeeeeeee eeeeeeeeeeee, eee eee eeeee eeeeeeee ee eeee eeee eeee eeee eee eeeeeee eeeeeeeee, ee eeee (eeeeeeeeeeeeeeeee)eeeeee 88, eeeeeeee ee eee eeeeeeee ee eee(eeeeeeeeeeee)eeeeeeeeeeeeeeeee(MM) eee MMeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeee Meeeeeee ee ee (Meeeeeeeeee)eeeeeeeeeeeeeee eeee Meee eee Meeeeee Meeeeeeee[‌88‌]

Meeeeeeeeee 88

Me8 Meeee (%) Mee
Me 88 [‌88‌]
8-Mee 88 [‌88‌]
8-MeM8MM8M8 88 [‌88‌]
8,8-(MeM)8M8M8 88 [‌88‌]
88 [‌88‌]
88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

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M-(Meeeeeeeee)eeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

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8-Meeeeeeeeeeeeeee 88 ee M-(Meeeeeeeee)eeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

Me e Meeeeee eeeeeeeee eeee eeee eeeee Me(MMe)8 (8.8 ee, 8.8 µeee), MMeee (8.8 ee, 8 µeee), eee eeeeeeeeeeeeeeee (8.88 eeee), eee (eeeeeeeeeeeee)eeeeeeeeeeeeeee (8.88 eeee) ee eee (eeeeeeeeeeeeeeeee)eeeeeeeeeeeeeee eeee (8.88 eeee), eee M8MM8 (888 ee, 8.88 eeee). Mee eeee eee eeeeee eeee e MMMM-eeeee eeeeee eee eeeeee eeee M8 (8 ×). Me eee eeeeeeee eeeeee eee eeeee e eeeeeee ee e-MeMM eee M8M (8:8; 8.8 eM), eee eee eeeeeee eee eeeeee ee 888 °M eee 8–88 e. Mee eeeeeee eee eeeeeee ee eeee ee ee eee eeeeeeeee eeee MeMMe (8 × 8 eM), eee eee MeMMe eeeeeeee eeee eeee eeeee (MeMM8). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeee eeeeeeeeeeeeee (eeeeee eee).

M-(eeee-Meeeeeeeeeeeee)-8-eeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

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M-(Meeeeeeeee)eeeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeeeee eeee eeeeeeee eeee e eeeeeee eee eeee eeeee MeMe8(MMMe)8 (8.8 ee, 8 eee%), MeMeee (8 eee%), Me8MM8 (8 eeeee), eee eee (eeeeeeeeeeeeeeeee)eeeeeeeeeeeeeee (8–8.8 eeeee). Mee eeee eee eeeeee eeee e MMMM-eeeee eeeeee eee eeeeee eeee M8 (8 ×). Mee eeeeeeeeeeee (8.88 eeee, 8 eeeee) eee eeee eeeee eeeee e eeeeeeeeeeee, eee eeee e-MeMM eee eeeeeeee eeeeeeeee M8M eeee eeeee. Mee eeeeeee eee eeee eeeeee eeee e eeeeeeeee eee eeee eee eeeeee ee 888 °M eee 88–88 e. Mee eeeeeee eee eeeeeee ee eeee ee ee, eee eeee eee eeeeeeee, eee eee eeeeeee eee eeeeeee eeee MeMMe (8 eM) eee M8M (8 eM). Mee eeeeeee eeeee eee eeeeee eeeeeee e Meeeee eeee eee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee ee eeeee eeeeeee).

(Meeeeeeeeeeeeeeee)eeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

Meee e Meeeeee eeeeeeeee eeee eeeeeeee eeee e eeeeeee eee eeee eeeee eeeeeeeee (eeeeeeeeeeeeeeeee)eeeeeeeeeeeeeee (88; 88.8 ee, 8.8 eeee), M8MM8 (888 ee, 8.88 eeee), MeMe8(MMMe)8 (8.8 ee, 8.8 eee%), eee MMeee (88.8 ee, 88 eee%). Mee eeee eee eeeeee eeee e MMMM-eeeee eeeeee eee eeeeee eeee M8 (8 ×). Mee eeeeeeeeeeee (8.88 eeee, 8.8 eeeee) eee eeeee eeeee e eeeeeeeeeeee, eee eeee e-MeMM (8.8 eM) eee eeeeeeee eeeeeeeee M8M (8.8 eM) eeee eeeee. Mee eeeeeeeee eeeeeee eee eeeeeee ee 888 °M eee 8–88 e. Meeee eee eeeeeeee eee eeeeeeee (eeeeeeeee ee MMM), eee eeeeeee eee eeeeeee ee eeee ee ee, eee eeee eee eeeeeeee, eee eee eeeeeee eee eeeeeee eeee MM8Me8 (8 eM) eee M8M (8 eM). Mee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (8 × 88 eM), eee eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee eee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee).

References


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