Science of Synthesis

Zaidlewicz, M.; Krzeminski, M., Science of Synthesis, (2005) 6, 1098.

Hydroboration is defined as the addition of a B—H bond across a C—C multiple bond to give an organoborane (‌Scheme 5‌).[‌1‌,‌23‌]

‌Meeeee 8‌ Meeeeee Meeeeeee eee Meeeeeeeeeeee[‌8‌,‌88‌]

Meeeeeee eeeeeeee eeeeee eeeeeeeeee eeee eeeeeee, eee eeeeeeee ee eeeeeeeee ee eeeeee. Mee eeeeeeeee eeeeee ee eeeeeeeeee ee eee eeeeeeeee eeee eeeeeeee ee eeeeee eeeeee, eee eeeee eeeeeee eeeeeeeeeee eeeeee/eeeee eeeeeeeee (‌Meeeee 8‌).[‌88‌,‌88‌]

‌Meeeee 8‌ Meeeeeeeeeee ee Meeeeeee ee Meeeeeee Meeeeeee[‌88‌,‌88‌]

Meeeee eeeeeee eeee eeeee Meeee eeeee, eeee ee eeeeeee eeeeeeee,[‌88‌–‌88‌] eee eeeeeee eeeeeeee eeeeeeee eeeeee,[‌88‌–‌88‌] eee eeee eeeeee eeeeeeee eeeeeeeeeeeee eeeeeee ee eeee eeeeeeeeeee. Mee eeeeeeeee eeeee ee eeeeeeeeee ee eee eeeeeee eeeeee eee-8-eee ee eeeeeeee: eeeeee–eeeeeeeeeeeeeee > eeeeee–eeeeeeee eeeeeee, eeeeee–8,8-eeeeeeeee > eeeeee–eeeeee. Meeeeeee eeeeeee eeee eeeeeeeeee eeeeeeee eeeeee eee eeee eeeeeeee eee eeeeeeeeeee eeeeeee ee eeeeeeee eeeeeeeeeeee eeee eee eeeeeee eeeeeeeeee.[‌88‌–‌88‌] Meeeeeeeeeee ee eee eeee eeeeeeeee eeeeee eee eee eeeeeeee eeee ee eeeeee ee eeeeeeeeeee ee e eeeeeee eeeeeeeee eee eee eeeeeeeeeeeeee eeee eeeeee/eeeeeeee eeeee eeee eeeeeeeee.[‌8‌,‌88‌,‌88‌] Mee eeeeeeeeeeeee ee eeee eeeeeee eeee eeeeee–eeeeeeeeeeeeeee eee eeeeee–eeeeeeee eeeeeee eeeeeeeee eeeeeeee eeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeeeeeeee. Meeeee eeeeeeeeee eeeeeee eeeee eeeeeeeeeeeeeee eee ee ee eee eeeeeeee ee eeee eee eeeeeeee ee eee eeee- ee eeeeeeeeeeeee eeeeee (‌Meeeee 8‌).

‌Meeeee 8‌ Meeeeeeeeeeee ee Meeeeeeeee Meeeeee

Meee eeee eeeeeeee eeeeeee eee eeeeeeee eee ee eeeeeeeeee ee eeee eeeeee ee eee eeeeeee- ee eeeeeeeeeeeeeee eeeee. Mee eee eee eeeeeeee eeeeeeeeee eeeeeee eeee eee eeeeeeeee ee eee eeeeee; eee eeeeeee, β-eeeeee eeeeee eeeeeee ee eeee eee-eee-eeeeeeeeeeeeee,[‌8‌] eeeeeee eeee eeeeeeee eeeeeeeeeee eeeee eeeeeeeeeeee eeeeee.[‌88‌] Meeeeeeee, ee eeeeeeee ee eeeeeeeeeeee, eee eeeeeeeeeeeee ee eeeeeeeeeee eee ee eeeeeee eeeeeeeeee ee eeeee eeeeeeeeeeeeeeeeee;[‌8‌] eeeeeeeeee eeee ee eeeeeee ee eee eeeee eeeeeeeeee ee eeeeeeeeeee eee eee eee eeeeeeeeee ee eeeeeeeeeeeeeeeeee. Meeeeee eeeeeeeeeeeeee eeeeeee, eee eeeeeee, 8-eeeeeeeee-8-eee, α-eeeeee, 8- ee 8-eeeeee, eee eeeeeee eeeeeeeee eeee eee(8,8-eeeeeeeeeeeeee)eeeeee (eeeeeeeeeeeeee, Mee8MM),[‌8‌] eeeeeeeeeeeeeeeeeeeeeee (Mee8MM),[‌88‌] 8- ee 8-eeeeeeeeeeeeeeeeeee (8-Mee8MM, 8-Mee8MM),[‌88‌] eeeeeeeeeeee (‌Meeeee 8‌). Mee eeeeeeeeeeeee ee 8-eeeeeeeeeee eeeeeeeeee eee ee eeeeeeeeee ee eeeeeee eeeeee ee eee eeeeeeeeeeeee eeeee, eee eeee eeeeeeeeee eeeeeeeee eeeee eeeeee (Me, Me), ee ee eee eeeeeeeeeeeeeee eeeee eee eee eeee eeeeeeee eeeeee (eMe, eMe, Me).[‌88‌] Meeeeeeeeeeeeeee eeeeee eeeee, eeeee eeeeeee ee eee eeeeeeeeeeeeeee eeeee, eeeeeee eeeeeeee eeeee eeee eeee, eee eeeeeee, 8,8-eeeeeeeeeee-8-eee ee eeeeeeeeeee eeee (8,8,8-eeeeeeeeeeeeeee)eeeeee (eeeeeeeeeeee, MeeMM8).[‌8‌]

‌Meeeee 8‌ Meeeeeeeeeeeee Meee- eee Meeeeeeeeeeeee Meeeeeee ee Meeeeeeeee Meeeeeeeeeeee

Me eeeeeee eeeee, ee ee eeeeeeee ee eeeee eee eeeeeeeeeeeee eeeeeeee ee ee e eeeeeeeeee eeeee, eeeeeeeee eeeeeeeee eeee ee eeeeeeeeeeeeeeeeeee, eeee(8,8-eeeeeeeeeeeeee)eeeeee, ee eee(8,8,8-eeeeeeeeeeeeeee)eeeeee, ee eeeeeeeee eeeeeeeeee eeeeeeeeeeee eeeeeeeee, eeee eeeeeeee eeeee, ee eeeeeeeeeeeeeee.[‌88‌–‌88‌] Me eee eeee ee eeeeeeeeee eeeeee eeeee eeeee eeeeee eeeeeeeeeeee eee ee eeee ee eeeee eee eeeeeeee ee eeeeeeeeee, eee eeee eeee ee eeeee ee eeeee eeeeeee eeeeeeeeeeeee ee eee eeeeeeeeeeee. Me eeee eeeeeeeee ee eee eeee eeeee eeee eeeeeeeee eeeeeeeeee eeeeee eeeee eeeeee eeeeee eeeeee eee eeeeeeeee, eee eeeeeee, 8α-eeeeeee-8(88)ee-8β-ee, eeee ee eeeeeee eeeeeeeeeeeee.[‌88‌] Meeeeee, eeee eeeeee eeeee eee eeeee eeeee eeee eeeeeee eeeeeeeeee. Meee- eee eeeeeeeeeeeeee eee eeeeeeee eeeeeeeeeeeee eeeeee eeeeeeeee eeeee eeeeee ee eeeeeeeeeeeeeee eeee eeeeeeeee eeeee eeeeee. Meee eeeeeee eeeee ee eeeeeee eeeeeee eee-eeeeeeeeeeeeeeee eee eee-eeeeeeeeeeeeeeeeeee. Mee eeeeee eeeeeeeee eeeeeeeeee eeee eeeeeeee, eeeee eeeeeeeeeeee eeeee eeee ee eeeeee. Meee eeee eeeeeeee eeeeeeeeeeee, eee eeeeeee, eee(8,8,8-eeeeeeeeeeeeeee)eeeeee eee eee(8-eeeeeeeeeeeeeeeeeeee)eeeeee, eee eeeeeeeee.[‌88‌] Meeeeee, eee eeeeeeeeeee ee eeeeeeeeeeee, eeeeeeee eee eeeee ee eee eeeeeeeee eeeeeeeeee eeee eeeeeee eeeeee eee eeeeeee eeeeeeeee ee eeeeeeeee ee eeeeeeee eee eeeeeeee.

Meeeee eee-8-eeee eeeee eeee eeeeee–eeeeeeeeeeeeeee eee eeeeee eeeeeee eeee eeeeeee eeeeeeee eee eeeeeeee eeeeeeee eeeeee eeeeeee 88% ee eee eeeee ee eee eeeeeeee eeeeeeee eee 8% ee eee eeeeeeeee eeeeeeee (‌Meeeee 8‌).[‌88‌] Me eeeeeee eeee eee eeeeeeeeeeeee eeeeeeee eeeeeeee e eeeeee eeee-eeeeee eeeeeeeeee eeeee eeee eee eeeeeeeee ee eeeeeeee eeeeeeeeee eeeeeeeee ee eee eeeeeeeeeeee ee eee M—M eeee.

‌Meeeee 8‌ M Meeeee Meee-Meeeee Meeeeeeeee Meeee ee eee Meeeeeeeeeeee Meeeeeee[‌88‌]

Meee 88:8 eeeeeeeeeeee ee ee eeeeeee ee eeeee eeeeeeeeee eeeeeeeeeeeee eeeee ee eeeeeeeeee eeeeeeeeeeeeeeee. Mee eeee eeeeeeee eeee eeeeee ee eee eeeeeeeeeeeeee ee eeeeeeeeee. Meeeeee, eee eeee eeee 8% eeeeeeee ee eee eeeeeeeee eeeeeeee eeeeee eeeee eeee eee eeeeeeeeeeeeee eee eeeeeee ee ee 88% ee e (eeeeeee)eee-eeeeeeeeeee. Meee eee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeeee eeeeeeeee eeeeeeeee ee eeeee eeeeee. Me eeee eeeee, eeeeeeeeeeeee eeee eeeeee eeeeeeeeeeeeee eeeeeeeeeeeeee ee eeeeeeeee. Meeeeee eeeeee eeeeeeeee eeeeeeee ee eee eeeeeeee eeeeee eeee ee eee eeeeeee eeeeee eeee, eee eee eeeeeeeeeeeeeeee ee eeee eeeeeeee ee eeeeeeeeee ee eee eeeeee ee eeeeeeeeeeee ee eee eeeeeeee eeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeee ee Meeeeeeeeeeee ee Meeeeee eee Meeeeeeeeee Meeeeeee eeee Meeeee–Meeeeeeeeeeeeee Meeeeee[‌88‌]

Mee eeeeeeeeeeeeeeee ee eeeeeeeeeeeee ee 8-eeeeeeeeee eee 8-eeeeeeeeeeeeee eeee eeeeee–eeeeeeee eeeeeee eeeeeee ee eeeeeee ee eeee eeeeeeee eee eeeeeee (‌Meeeee 88‌).[‌88‌] Mee eeeeeeeeeeeeee ee eeeeeeeee eeeeee ee eee eeeeeeeee eeeeeeeeeeee ee eeeeee eee ee eee eeeeee eeeeeeeee eeeeee ee eee eeeeeeee eeee eeeeeeeee ee eeeeee.

‌Meeeee 88‌ Meeeeeeeeeeeeeee ee eee Meeeeeeeeeeee ee Meeee Meeeeeeeeee ee Meeee, Meeeeeeee, ee Meeeeeee eeee Meeeee–Meeeeeee Meeeeee Meeeeee[‌88‌]

Meeeeeeee eeeeeee ee eee eeeeeeeeeeeee ee eeeeeee eee eeeee eeeeeeeeeeeeee eeeeeeeeeee ee eeeeee–eeeeeeeeeeeeeee eee eeeeeeeeeeeeee eee eeee eeeeeeeeeee;[‌88‌,‌88‌,‌88‌–‌88‌] eeee eeeeeeeeeeeeee eeeeeeee eee eeeeeeeee ee ‌Meeee 8‌. Meeeeeeeeeeee eeeeeeee eeeeeee eeeee eeee eeeeee–eeeeeeeeeeeeeee eeeeeee eee eeeee eeee ee eee eeeeeeee eeeeeeee eeee eeee eeeeeeeeeee. Me eee eeeee eeee, eeee eeeee eeeeeeeeeeeeee ee eeeeeeee eeeeeee eee eee eeeeeeeee ee ee eeeeeeee eeeeeeeeeeeee eeeeee (e.e., 8-eeeeeeeeee-8-eee) eeeeeeeeee eeeee eeeeee ee eeeeeeeee eeeeee eeeeeeeeeeee. Meeeeee, ee ee eeeeeeee ee eeeeeee eeeeeeeee eeeeeeeeeeeee ee eeee eeeeeee ee eee eee ee eeeeeeeeee eeeeeeeee eeeeeeeeeeeeee. Meeeeeeeee eeeeee eeeeeeeee eee eeeeeeeeeeeeeeee ee eeeeeeeeeeeee ee eeeeeeeee, eeeeeeeee, eee eeeeee eeeeeee, eeeee eeeeeeeee eeeeeeeee ee eee eeeeeeeee ee eee eeeeee eeee eee eee eeeeeeeeee eeeee. Me eeeeeeeee eeeeeeee ee eeeee ee eee eeeeeeeee eeeeeeee (88–88%) ee eeeeeeee eee eee-8-eeee eeeeeeeeeee.[‌88‌] Me eeeeeee eeeeeee eee eeeeeeee ee eeeeeeee-eeeeeeeeeee eeeeeeeeeeee eeeeee eee eeeee eeee ee eee β-eeeeeeee; eeee ee eeeeeeee ee eee eeeeeeeeeeeeeeeee ee eee eeeeeeeeeee ee eeeeeeeee.[‌88‌,‌88‌] Meeeeee eeeeeeeeeeee eeeeee e eeeeee eeeeeeee-eeeeeeee eeeeee, eee eeeeeee, eeeeee (MM8) ee eeeeeeeee eeeee (MM88), eeeeee eeeee ee eee β-eeeeeeee.[‌88‌] Mee eeeeeee ee eeeeeeee eee eeeeeeeeeeee eeeeeee eeeeeee ee eeeee eeeee.[‌88‌–‌88‌] Mee eeeeeee, eee-eeeeeee eeeeeeeee eee eeeeeeee ee eeeeeeeeeeeeeee ee eeeeeeee eeeeeee eeee eeee eeeee eeeeeeeeeeeeee eeee ee eeeeeeeeeeeeeeeeee.[‌88‌]

‌Meeee 8‌ Meeeeeeee Meeeeee ee eee Meeeeeeeeeeee ee Meeeeeeeeeeeee Meeeeee eee Meeeeeeeeeeeee Meeeeee eeee Meeeee–Meeeeeeeeeeeeee, Mee(8-eeeeee-8-eeeee)eeeeee, eee 8-Meeeeeeeeee[8.8.8]eeeeee[‌88‌,‌88‌,‌88‌–‌88‌,‌88‌–‌88‌]

Meeeee	Meeeee Meeeeeeeeeee (e/e) (%)			Mee
	MM8•MMM	Mee8MM	8-MMMM
	8:88	8:88	8.8:88.8	[‌88‌,‌88‌,‌88‌]
	88:88	8:88	8:88	[‌88‌,‌88‌,‌88‌]
	8:88		8.8:88.8	[‌88‌,‌88‌,‌88‌]
	88:88	8:88	8.8:88.8	[‌88‌,‌88‌,‌88‌]
	8:88		8.8:88.8	[‌88‌,‌88‌,‌88‌]
	88:88	8:88	8.8:88.8	[‌88‌,‌88‌,‌88‌–‌88‌]
	88:88	8:88	8.8:88.8	[‌88‌,‌88‌,‌88‌–‌88‌]
	88:88	888	888	[‌88‌,‌88‌,‌88‌–‌88‌]
	888		888	[‌88‌,‌88‌,‌88‌–‌88‌]
	88:88		888	[‌88‌,‌88‌,‌88‌–‌88‌]
			88:88	[‌88‌,‌88‌,‌88‌,‌88‌–‌88‌]
	88:88	8:88	888	[‌88‌,‌88‌,‌88‌,‌88‌–‌88‌]

Mee eeeeeeeeeeeee eeeeeeee eeeeeeee eee-eeeeeeee ee eee M—M eeee ee ee eeeeee ee eeeeeeeeeeee ee e eeeee eeeeee ee eeeeeeeeeeeee–eeeeeeeee eeeeeeeee. Meeeeeeee ee eee M—M eeee eeee eeeeeeee eeeeeeee eeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeee (‌Meeeee 88‌).[‌8‌]

‌Meeeee 88‌ Mee eee-Meeeeeee ee eee M—M Meee ee eee Meeeeeeeeeeee ee 8-Meeeeeeeeeeeeeeee[‌8‌]

eee-Meeeeeee eee eeee eeee eeeeeeeeeeee eeeeeeee ee eee MMM eeeee ee eeeeeeeeeeeeeee eeeeeee eeee eeeeeeeeee eee-8-eee eee eeeeeeeeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Mee eee-Meeeeeee ee eee M—M eee M—M Meee ee eee Meeeeeeeeeeee ee Meeeeeeeee Mee-8-eeee[‌88‌]

Mee eeeeeeeeeeeee–eeeeeeeee ee eeeeeeeeee eeee eeeeee–eeeeeeeeeeeeeee eeeeeee eeeeee eee-8-eeeeeeeeee eeeeee eeeeeeeeeee, eeeeeeeeee eee eeeeeeee ee eeeeee eeee eee eeee-eeeeeeee eeee ee eee eeeeee eeee (‌Meeeee 88‌).[‌8‌,‌88‌]

‌Meeeee 88‌ Mee eee-Meeeeeeee Meeeeeee ee Meeeee ee Meeeeeeeee[‌8‌,‌88‌]

Meeeee eeeeeeeeeeeee eeee eeeeeee eeeee eeeeeeeee eeeeeeeeeeeee ee eeeeee eeeeeeeee. Meeeeee eeeeeeeeeee eeeeee ee eeeee eeeeeeeeeeeeeeeee ee eeeeeeee ee eee eeeeeeeeeeeee ee eeeeeeee eeeeeeeeeeeeeeeee.[‌88‌,‌88‌] Meeee, eeeeeeeeee eeeeeeeee eeeeeeeeeeeee eeeeee eeee eeeeee eeeeeeeeeeeeeeeee. Meeeeeeeee eeeeee eee eeeeeeeee eee eeeeeeeeeeeeeee ee eeeeeeee. Mee eeeeeee, eeeeeee eeeeeeeeeee eeeeeeee eeeeee eeeeee eee eeee ee eee eeeeee eeee eeee eeeeeeee ee eeeeee eeeeeeeeeeee ee eeeeee eeeeeee eeeeeeeeeeeee eeee eee eeeeeeee eeee.[‌88‌] Me eeeeeeee, eeeeee eeeeeeeeee eeeeee, eeee ee eeeeee, eee eeeeeeeeee eee eeeeeeee eeee eee eeee eeee.[‌88‌,‌88‌] Meee eeeeeeee eeee eeeeeeeeee eeeee eeeeeeeeeee eeeeeeeeeee eee eeeeeeeee eeeeeeee ee ‌Meeeee 88‌.[‌88‌,‌88‌,‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeeee ee eee Meeeeeeeeeeee ee Meeeeeee Meeeeeee Meeeeee[‌88‌,‌88‌,‌88‌]

Meeee eee eeee eeeee eeeeeeeeeeeeee eeeeeeeeeeee eeee ee eee eeeeeeeeeeeeee eeee eeeeeeeeeeeee eeeeeeee ee ee eeee-Meeeeeeeeee eee-eeeeeeee eeee eee eeee-eeeeeeee eeee ee eee eeeeee eeee.[‌88‌] Meeeeee eeeeeee ee eeee eeeeeeee ee eee eeeeeeeeeeeee ee eeeeee 8,8-eeeeeeeeeeeeeeeeeee ee (−)-β-eeeeee (‌Meeeee 88‌).[‌88‌,‌88‌]

‌Meeeee 88‌ Meeeeeeee ee eee Meee Meeeeeeeeeeeeeeee Meeeee Meeeeeee ee eee Meeeeeeeeeeee ee 8,8-Meeeeeeeeeeeeeeeeee eee (−)-β-Meeeee[‌88‌,‌88‌]

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8e, 88.
• 8.Meeeee-Meee, (8888) 88/8e, 88.
• 8.Meeeee-Meee, (8888) M 88e, 888.