Science of Synthesis

Kitching, W.; Glenn, M., Science of Synthesis, (2004) 3, 257.

Organoboron reagents are generally less reactive to mercury(II) derivatives than the alkali metal reagents discussed vide supra, but are of considerable use, principally due to their ready availability and wider tolerance of functionality. Despite the reduced reactivity, a wide range of mercury(II) derivatives has been prepared and include alkyl, benzyl, vinyl, and aryl systems. Discussion of the preparation of vinyl systems can also be found in Section ‌3.3.3.8‌.

Meeeeee eeeeeeeeeeeeeee eeeeeeee eeee eeeeeeeeeeee eeeeee ee eeeeeeeeeeee(MM) eeeeeeeee, eeeeeeeee e eeeeee eeeeeeeeee eeeee ee eeeeeeeeeeee(MM) eeeeeee eee eeeeeeeeeeeee ee eeeeeeee eeeeeee, e.e. 8,8-eeeeeeeeeee-8-eee (‌888‌) eeeee eee(8,8-eeeeeeeeeeeee)eeeeeee(MM) (‌888‌) eee 8-eeeeeeeeeeeeeeee (‌888‌) eeeee eee(8-eeeeeeee-8-eeeeeeeee)eeeeeee(MM) (‌888‌) (‌Meeeee 888‌).[‌888‌,‌888‌,‌888‌] Me eeeeeee, eeeeeeeeeee ee eeeeeeeee eeeeeeeeeeee ee eeeeeeeee[‌888‌] eee eeeeeeee eeeeeeee eeeeeeeeeeee eee eeeeeeeee eeeeeeee eeeee ee eeee eeeeee eee ee ee eeeeeeee. Meee eeeeeeeeee eeeeeeeeee ee eeeeeeeeeeee eeeeee eee eee eeeeeeeee eeeeeeeeeeeee–eeeeeeeeeee ee eeeeee eeee eeeeeee eeee ee eeeeeeee eee e eeeeeeee eeeeee.[‌888‌] Meee eeeeee ee eeeeeeeee eeeeeee(MM) eeeeeeeeeee eee ee eeeeeeee ee eeeeeeee ee eee eeeeeeeeeee eeee eeeeeee(MM) eeeeeeeeee, eeee eeeeeeeee eeeeeeee eeeeeeeeee ee e eeee-eeeeeee eeeee eeeeeeeee.[‌888‌]

‌Meeeee 888‌ Meeeeeeeeeeee–Meeeeeeeeee ee 8,8-Meeeeeeeeee-8-eee eee 8-Meeeeeeeeeeeeeee ee Meeeeeee ee Meeeeeee Meeeeee[‌888‌,‌888‌]

Mee eeeeeeeeeeeeee eeeeeeeeeee ee eeeeeeeeeeeee–eeeeeeeeeee ee eeeeeeee eeeeeee eeeeeeee eeee(eeeeeee-8,8-eeeeeeeeeeeee-8,8-e8)eeeeee (‌888‌), eeeeeeeee eeee eeeeeeeeeeeee ee (M)-8,8-eeeeeeeeeee-8-eee-8-e8 (‌888‌) eeee eeeeeeeeeeeee–eeeeee eeeeeee eeeeeee.[‌888‌] Meeeeeee ee eee eeeeee ‌888‌ eeee eeeeeee(MM) eeeeeee eeeeeeee eeee >88% eeeeeeeee ee eeeeeeeeeeeee eeeeee ‌888‌, ee eeeee ee ‌Meeeee 888‌. Meeee eeeeeee eeeeeee eeeeeee eeeeeee.[‌888‌]

‌Meeeee 888‌ Meeeeeeeeeeeeee ee Meeeeeeeeeeee–Meeeeeeeeee ee Meeeeee Meeeeee[‌888‌]

Mee eeeeeeeeeeeeee eeeeeeeeeeee ee eee eeeeeeeeeee ee eeeeeeee[(M)-8-eeeeeeeeeee]eeeeee (‌888‌)[‌888‌] eee eeee(eeeeeee[8.8.8]eeee-8-eee-ee]eeeeeee (‌888‌)[‌888‌] eeee eeee eeee eeeeeee ee eeeeee eee ee eeeee eeeee eeeeeeeeeee eeeeeeee ee eeee [(M)-8-eeeeeeeeeee]eeeeeee(MM) eeeeeeee (‌888‌) eee [eeeeeee[8.8.8]eeee-8-eee-ee]eeeeeee(MM) eeeeeee (eee-‌888‌), eeeeeeeeeeee, eeee eeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeee (‌Meeeee 888‌). Meeeeee eeeeeeeee ee eee eeeeee eeeeee eee eeeeeeee ee eeeeeeeeeeee ee eee eeeeeee.

‌Meeeee 888‌ Meeeeeeeeeeeeee ee Meeeeeeeeeeee–Meeeeeeeeee ee Meeeeeeee Meeeeee[‌888‌,‌888‌]

Me eeeeeeee ee eeeeeee, eeee eeeeeeee eee eeeeeeee eeeeeee eeeeeee eeeeee eeeeeeeeeeeee–eeeeeeeeeee ee eeeeeee eeeeeeeeeeee(MM) eeeeeeeee ee eeeeeeeee eeeeee.[‌888‌,‌888‌,‌888‌] Meeee eeeeeeeee eee eeee eeeeeeee eeee eeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeee (8,8,8-eeeeeeeeeeeeeeee) ee eee eeeeeeeeeeeee eeeee, eeeeeeee eee eeeeee ee eeeee ee eeee eeeeeeeeeeeeeeeee ee e eeee eeeeeeee eeee eeeeeeeee ee eee eeeeeeeeee eeeeee.[‌888‌] Meeeee eeeeee eee eeee eeeeeeee eeee 8,8,8-eeeeeeeeeeeeeeeee, eee eeee ee eee eeeeeee ee eeeeee eee eeeeeeeeeeeee ee eeeeeeee eeeeeee. Mee eeee Meeeeeee ‌8.8.8.8‌ eee ‌8.8.8.8‌.

Mee eeeeeeeeeeeeee eeeeeeeeeeeeee ee eee eeeeeeeee eeeeeeeeeeee(MM) eeeeeeeee eeee eeee eeeeeee ee eeee eeeeee, eee ee eee eeeee ee eee eeeeeeee 888Me—8M eeee–eeee eeeeeeee eeeeeeeee, eee eeeeeeee eee (M)-eeeeeeeeeeee(MM) eeeeeee, eeeeeeeeeee eeeeeee ee eee eeeeeee ee eee eeeee eeeee 8MMe—M eeeeeeee eeeeeeeee eeeeeeee ee eeeeeeeeeeee(MM) eeeeeee.[‌888‌] Meeeeeeeeeee ee eee eeeee eeee eee eeeeeeeeeeee eeeeeeeeeeee eeeee ee eeee eeeeee eeee M eeeeeeeeeeeee eee ee eeee eee eeeeeeee eeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeee, eeeeeeeeee ee ee >88%. Meeeeeee eee eee eeeeeeee ee 8-eeeeeeeeee-8-eee (‌888‌) ee 8,8-eeeeeeeeeeee-8-eee (‌888‌) eeee eeeeeeeeeeeeee ee eeee eee eeeeeeeeeeeee M-eeeeeee ‌888‌ eee ‌888‌ eee eeeee eeeeeeee eeee eeeeeee(MM) eeeeeee/eeeeee eeeeeeee ee eeee (M)-8-eeeeeeeeee-8-eeeeeeeeeee(MM) eeeeeeee (‌888‌) eee (M)-8,8,8-eeeeeeeeeeee-8-eeeeeeeeeee(MM) eeeeeeee (‌888‌) (‌Meeeee 888‌).[‌888‌]

‌Meeeee 888‌ Meeeeeeeeeee(MM) Meeeeee eeee Meeeeeeeee, Meeeeeeee Meeeeeeeeeee Meeeeee[‌888‌]

Meeeeeeeeee eeeee eeee eeeee eeeeeeee eee eeeeeeeeeeeeee eeee eeeeeee(MM) eeeeeeee ee eeeee eeeeeeeeeee(MM) eeeeeeeee (eeeeeeeee ee Meeeeee ‌8.8.8‌). Mee eeeeeee eeeee eeeeeeee eeeeeee 8-eeeee eee eeeeee,[‌888‌] ee eeee ee eee 8-eeeee eee 8-eeeeeee eeeeeeeeeee.[‌888‌] Meeeeeeeeeeee eeeeeee(MM) eeeeeeeeeee ‌888‌ eee eeee ee eeeeeeee ee eeee eeeeee (‌Meeeee 888‌, eeeeee eee eeeeee eeeeeeeeee).[‌888‌,‌888‌]

‌Meeeee 888‌ Meeeeeeee ee Meeee Meeeeeeeeeeeeee(MM) Meeeeeeee[‌888‌,‌888‌–‌888‌]

Mee eeeeeeeee ee eeeeeeeeeeeee(MM) eeeeeee eeee eeeeeee ee eeeeeeeee eeeeeeee ee eeeeeeeee ee eee eeeeeeeeeee eeeeee ee eeeeeeeeeeeeeee eeee eeeeeee(MM) eeeeeee, eeeee ee eeeeeeeee ee eeeeee eeeeeeee eeeeeeee eeeeeee eee eeeeeeeeeeeee(MM) eeeeeeee. Meeeeeeeeeeee eeeee, eeeeeeeee eeeeeeeeeee eeeee eeeee eeee ee eeeeeee eeeeeee(MM) eeeeeeee eeeeeeee ee eeeeeee eee eeeeeeeeeeeee eeeeeeeeeeeee(MM) eeeeeeee eeeeeeee. Meeee eeee eeeeeeeee eeee eeeee ee eeeeeee eeeeeee eee eeeeeeeeeeeeeee ee eeeeeeeeeeeee eeeeeeee eeeeeeeeeeeee.[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeeeeee(MM) Meeeeeee; Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee eeeeeeeee(8-eeeeeeeeeeeee)eeeeee (8.8 e, 8.8 eeee) ee M8M (888 eM) ee 88 °M eee eeeee e eee. eeee ee MeMe8 eeeee ee eeeeeee eeeeeeeeeeeee eeeeeeee. Meeee 88 eee eee eeeeeeeeeee eee eeeeeeee, eee eeeeee eeee eee M8M ee eeeeee eeeeee MeMe8. Mee eeeee eee eeeeeeeeeeeeee (88% MeMM) ee eeee eee eeeeeee ee e eeeee eeeeee; eeeee: ∼888%; ee 888.8–888.8 °M.

(8-Meeeeeeeeeee)eeeeeeeeeeeee(MM); Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee 8-eeeeeeeeeeeeeeeeeee(MM) eeeeeee (8.88 e, 88 eeee) ee eeeeeee MeMM (88 eM) eee eeeee e eee eeee ee eeeeeeeee(eeeeee)eeeeee (8.8 e, 88 eeee) eee MeMM (8.8 e, 88 eeee) ee M8M (88 eM). M eeeee eeeeeeeeeee eeeeee eeeeeeeeeee. Mee eeeeeee eee eeeeee, eeeeeeee, eee eee eeeee eeeeee eeee M8M eee eeeee. Meeeeeeeeeeeeeeee (eeeeeeeee eeeee/eeeeeeeeeee) eeeeeeee eeeee eeeeeeee ee eee eeeeeee; eeeee: 8.8 e (88%); ee 888–888 °M.

Meeeeeeeeeee(MM) Meeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee 8 M MM8 ee MMM (888 eM) ee 8 °M eee eeeee eeee (8 °M) eeeeeeeeeee (88.8 e, 8.8 eee) eee eee eeee eee eeeeeee ee eeee eee 8 e. Mee-8-eee (8.8 eee) eee eeeee ee eee eeeeeeeee eeee ee eeeeeeeeeeeeeeeeee eee eeeeeeee eee eeeeeeeee eeeeeeeee ee ee. Me(MMe)8 (88.8 e, 8.8 eee) eee eeeee ee eee eeeeeeeee eeee ee (eeeeeeeeeeee)eeeeeeeeeee ee 8 °M eeeee M8 eee eee eeeeeee eee eeeeeee eee eeeeeee eee, eee eeeeeeee eeeeeee eee eeeeeeee eeee eeee eee eeeeee eeee MMM; eee eeeeeee eeeee eeeee eee eeeeeeeee eee eee ee ee eeeeeeeee ee e eeeeeeeeee. Mee eeeeeeee, eee eeeeeeeeeeee(MM) eeee eeee eeeeeeee eee eeeeee eeee eee eeee M8M (888 eM) eeeeeeeeee MeMe (8.88 e, 8.8 eee). Meeeeeeeee ee eee eeeeeee eeeee, eee eeeeeee ee MMM eeeeeee e eeeee eeeee, eeeee eee eeeeee eeee eeee M8M, eee eeeeeee (8 × 888 eM) ee 8 °M (ee −88 °M eee eeeeeeeeeeee(MM) eeeeeeeee eeeeeee eeee eeeeeeee eeeeeee. Mee eeeeeee eee eeeee eeeeeeeee eeeee eeeeee, eee eeeee ee eeeeeeeeeeeeee (MeMM); eeeee: 88–88%.

(M)-Meee-8-eeeeeeeeeee(MM) Meeeeeee: eeeee: 88%

(M)-8-Meeeeeee-8-eeeeeeeeeeeeeeee(MM) Meeeeeee: eeeee: 88%

(M)-Meeeeeeeeeeee(MM) Meeeeeee: eeeee: 88%.

(M)-8-Meeeeeee-8-eeeeeeeeeee(MM) Meeeeeee: eeeee: 88%.

Meeeeeeeeeeeee(MM); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeee eeeeeeeeeeeeee(MM) eeeeeeeeeee eee eeeeeeee eee eeeeeeeee eeeee.

Me e eeee ee 8 M MM8 ee MMM ee 8 °M eee eeeee eeee (8 °M) eeeeee eee eee eeee eeeeeee ee eeee eee 8 e (88–88% eeeeee ee eeeeeeeeeeeeee ee eeeeeeee eeee). Me(MMe)8 eee eeeee ee eee eeeeeeeee eeee ee eeeeeeeeeeeeee ee 8 °M eeeee M8. Me 88% eeeeee ee eeeeeeeeeeeeee eee eeee eeee eee eeeeeee eee eeeeeee eee 88 eee ee ee eeeeeeeee ee eee eeeeeeee eee 8 e. Mee eeeeeee eee eeee eeeeee eeee 8 M MeMM (8 ×) eee ee M8MM8 (8 ×). Meeeee (MeMM8), eeeeeee ee eeeeeee, eee eeeeee eeeeeeeeeeee ee eeeeeeeeeeeeeeeee (eeeeeee, −88 °M).

Meeeeeeeeeeeee(MM):

Meeeeeeeeeeeee (8.88 eee, 88% eeeeee) eee Me(MMe)8 (88.8 e, 8.8 eee) eee eeeeeeee eee 8 e ee eeee eee eeeeeee; eeeee: 88%.

Meeeeeeeeeeeeeee(MM):

Meeeeeeeeeeeeeee (8.88 eee, 88% eeeeee) eee Me(MMe)8 (88.8 e, 8.8 eee) eee eeeeeeee eee 8 e ee eeee eee eeeeeee; eeeee: 88%.

Mee(8,8-eeeeeeeeeeeee)eeeeeee(MM):

Meee(8,8-eeeeeeeeeeeee)eeeeee (8.888 eee, 88% eeeeee) eee Me(MMe)8 (88.8 e, 8.88 eee) eeeeeee ee ee eee 88 eee ee eeee eee eeeeeee; eeeee: 88%.

Meeeeeeeeeeeee(MM); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeee eeeeeeeeeeeeee(MM) eeeeeeeeeee eee eeeeeeee eee eeeeeeeee eeeee.

Me e eeee ee 8 M MM8 ee MMM ee 8 °M eee eeeee eeee (8 °M) eeeeeeeeeee eee eee eeee eeeeeee ee eeee eee 8 e. Meeeee eee eeeee ee eee eeeeeeeee eeee ee eeeeeeeeeeeeeeeeee eee eeeeeeee eee eeeeeeeee eeeeeeeee. Me(MMe)8 eee eeeee ee eee eeee ee eeeeeeeeeeeeeeeeeeeeeee eee eee eeeeeee eeeeeee eee 8 e. Mee eeeeeee eee eeee eeeeee ee −88 °M. Me e eeeeeeeeeee eeeeee (Meeeee M), ee eee eeeeeeeee ee eeeeeeeeee, eee eeeeeeee eeeeeee ee eeeeee ee eeeeeeeeeeee, eee e eeeeee eeee ee eeeeeeee eeeeeeee ee eeeeeeeee. Mee eeeeeeeee eeeee eeeeee eeee eeeeeeeeeeeeee (eeeeeee, −88 °M). Me ee eeeeeeeeeee eeeeee eeee eeeeeee (Meeeee M), 8 M MeMM eee eeeee (8 eeeee ee MeMM eee eeee ee eeeee) eeeeeeee ee eee eeeeeeee eeeeeeee ee 88% M8M8 (8 eeeee ee M8M8 eee eeee ee eeeee eeee 88% eeeeee). Mee eeeeeeeee eee eeeeeeeee ee e eeeee eeee ee eeeeeee eeee eeeeeeeee. Meeee eeeeeeeeee eee eeeeeee eeeee eeee M8MM8 eee eeeeeee eeeee eee eeeeeeeee, eeeee (eeeee MeMM8) eee eee eeeeeee eeeeeeee eeee eee eeeeeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeeee.

Meeeeeeeeeeeeeee(MM):

Mee eeeeee eee eeeeeeee eeee eeeee-8-eee (8.8 eee) eee Me(MMe)8 (88.8 e, 8.8 eee) eee eeeee. Meeeee M eee eeee ee eeeeee eee eeeeeee; eeeee: 88%.

Mee[88-(eeeeeeeeeeeeeee)eeeee]eeeeeee(MM):

Mee eeeeee eee eeeeeeee eeee eeeeee eeeee-88-eeeeee (8.8 eee) eee Me(MMe)8 (88.8 e, 8.88 eee) eee eeeee. Meeeee M eee eeee ee eeeeee eee eeeeeee; eeeee: 88%.

Mee(8-eeeeeeeeeeee) eeeeeee(MM):

Mee eeeeee eee eeeeeeee eeee 8-eeeeeeeeee-8-eee (8.8 eee) eee Me(MMe)8 (88.8 e, 8.88 eee) eee eeeee. Meeeee M eee eeee ee eeeeee eee eeeeeee; eeeee: 88%.

eeeeeee-8,8-Meeeeeeeeeeee-8,8-e8-eeeeeee(MM) Meeeeeee; Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee eeee(eeeee-8,8-eeeeeeeeeeeee-8,8-e8)eeeeee (8.88 e, 8.8 eeee) ee MMM (88 eM) eee eeeee Me(MMe)8 (8.88 e, 8.8 eeee), eee eee eeeeeeeee eeeee eeeeeeeeee eeeeeee eee 8 e ee 88 °M, eee eeee eeeeee eeee 8 M ee MeMe (888 eM, 8.8 eee). Mee eeeeeeeee eeeee eeeeeeeeee eee eeeeeee eeeeeeeee eee eeeeeee ee eeeee eee eeeeee eeee M8M. Mee eeeee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeeeeeeeeee (88% MeMM) eeeeeeee eee eeeeeee; eeeee: 8.88 e (88%); ee 888.8–888.8 °M.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8e, 88.