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33.5.4.1.1.1 Variation 1: Hydrophosphination under Basic Conditions

DOI: 10.1055/sos-SD-033-00794

Gaumont, A. C.; Gulea, M., Science of Synthesis, (2007) 33, 712.

The first base-induced hydrophosphinations of alkynes were performed by using alkali metal phosphides directly (‌Scheme 2‌).[‌16‌] The β-isomer with E stereochemistry ‌1‌ is obtained as the major product with minor amounts of ‌2‌, but a reversal of selectivity is observed in the presence of a secondary or a primary amine.

‌Meeeee 8‌ Meeeeeeeeeeeeeeeee eeeee Meeee Meeeeeeeee[‌88‌–‌88‌]

‌Meeeeeeeeee 8‌

M8 M8 Meee Meee (°M) Meee (e) Meeee (‌8‌/‌8‌) Meeee (%) Mee
Me Me e-MeMM 888 88 88:8 88 [‌88‌]
Me M MMM 88 8.8 8:8 88 [‌88‌]
MMe8 MMe8 e-MeMM 88 88 – 88 [‌88‌]
MMe8 M MeMe 88 88 8:8 88 [‌88‌]

Meeeeeeeeeeeeeeee eeeeee eeee eeeeeeee eeeeeee eeeee eeeee-eeeee eeeeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee eeee (eeeeeeeee eeeeeeeee) eee e eeeee-eeeeeeee eeeeeeee ee eeeeeee eeeeeeee eeeeeeeee ee eeee eee β-eeeeee eeeeeeeeeee.[‌88‌]

‌Meeeee 8‌ Meeeeeeeeeeeeeeeee eeeee Meeee-Meeee Meeeeeeeee[‌88‌]

Meeeeee eeeeeeeeee [M8 = (MM8)8Me, (MM8)8Me, MM8MM(Me)Me] eeeee eeee 8 ee 8 eeeeeeeeeee ee eeeeeeeeeeeeeee ee eeee eee eeeeeeeeeeeee eee(eeeee)eeeeeeeeee ee eee eeee eeeeeeee ee e eeeeee ee eee eeeeeeee ee eee eeeeeee eeeeeeeee (‌Meeeee 8‌).[‌88‌,‌88‌] Mee eeeeeeeeeeeeeeeee eeeeeee ee eee eeeeeeeeeeee eeeeeee ee eee eeeeeeeeee eeee. Meeeeeeee eeee-eeeeeeee ee e eeeeeeeee eeeeee (88 eee%) eeeeeee eee eeeee eeeeeeee ee eeeeeeeeeeeeeeeee ee 8,8-eeeeeeeeeeee-8-eee (88% eeeee).[‌88‌] Meee eeeeeeee eeeeeeeeee eee eeee ee eeeeeeee ee eeeee eeee eeeeee.[‌88‌] Meeee-eeeeeeeeeee eeeeeeeee eeeeeeeeee ee eeeeeeeeee eeee eee ee eeeeeeeeeee eeeeeeee eeeeeeeeeeeeeeee.[‌88‌,‌88‌] Meee eeeeeeeeeeeee eeeeeeeeeeeeeeee, eeeeeeeeeeeee ee eee eeee ee eeeeee, eeeeeeeee eee eeeee-eeeeee.[‌88‌,‌88‌,‌88‌] Meee eeeeee eee eeeeeeeeeeeeeee, eee eeeeeeee eeeeeee eee eeeeeeeeeeeee eeeeeeeeee ee eeeeeeeeee eeeeee ee eee eeeeeeee ee eeeeeeeeeeeee.[‌88‌]

Meeeeeeeeeee eeeeeeeee

(M)-Meeeee-8,8-eeeeeee(eeeeeeeeeeeeeeeee) (‌8‌, M8 = MMe8; M8 = M): Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee Me8MM≡MM (8.8 e, 88.8 eeee), Me8MM (8.8 e, 88.8 eeee), e 8 M eeee ee MeMe ee eeeeeee/Me8M (8.8 eM, 8 eeee), eee eeeeeee eeeeeeeee eeeeeee (888 eM) (MMMMMMM: eeeeeeeeee) eee eeeeeeee eee 88 e. Mee eeeeeee eee eeeeeee ee 88°M (88 eee) eee eee eeeee eeeee eeeeeee eee eeeeee eeeeeee eeeee eeee MeMM eee eeee eeeeeeeeeeee (eeeeeee/MeMM) ee eeee e eeeee eeeee; eeeee: 8.8 e (88%); ee 888–888°M.

References

[16] Meeeee, M. M.; Meeeeeeee, M. M., Meeeeeeeeee Meee., (8888), 8888.
[17] Meeeeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeeee, M. M., Meee. M. Mee. Meee. (Meee. Meeeee.), (8888) 88, 8888.
[18] Meeeeeeeee, M.; Meeeee, M. M.; Meeee, M.; Müeeee, M., Meee. Mee., (8888) 888, 888.
[19] Meeeeeeeee, M.; Meeeeeeeeee, M.; Meeee, M.; Müeeee, M., Meee. Mee., (8888) 888, 8888.
[20] Meee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888.
[21] Meeeeeeee, M. M.; Meeeee, M. M.; Meeeee, M.M.; Meeeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M., Meee. M. Mee. Meee. (Meee. Meeeee.), (8888) 88, 8888.
[22] Meeeeeee, M. M.; Meeeeeeeeeeee, M. M.; Meeeeeee, M. M.; Meeee'eeeee, M. M.; Meeeee, M. M.; Meeeeeeeeeee, M. M.; Meeeeee, M. M.; Mee'eeee, M.M.; Meeeeeeeeee, M. M.; Meeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888.
[23] Meeeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meee, M.; Meeeee, M. M., Meee. Mee. Meee. Me., (8888) 888, 888.
[24] Meeeee, M.; Meeeeeee, M. M.; Meeeee, M. M., M. Meeeeeeee. Meee., (8888) 888, 888.
[25] Meee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888.
[26] Meee, M. M., Mee. Meee. Mee., (8888) 8, 888.
[27] Mäeee, M.; Meeeeeee, M., Meeee. Meee., (8888) 88, 88; Meeee. Meee. Mee. Me. Meee. (8888) 8, 88.

Meeeeee Meeeeeeeeee

  • 8.Meeeee-Meee, (8888) M 8, 888.

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