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3.3.3.5 Method 5: Carbonylation

DOI: 10.1055/sos-SD-003-00211

Kitching, W.; Glenn, M.Science of Synthesis, (20043180.

Carbon monoxide is a valuable C1 source and its linking to organic groups attached to mercury is achieved using palladium and rhodium catalysts, as unassisted carbonylation requires high pressures and temperatures and it is not synthetically efficient. The catalysts appears to operate by forming organic derivatives by group transfer from mercury,[‌272‌] which experience CO insertion, and the aryl derivative may form products dependent on conditions, particularly solvent. The considerable background to this area has been reviewed.[‌141‌,‌268‌] As many of the reports describing carbonylation of organomercury(II) compounds include vinyl as well as aryl derivatives, reactions of the latter are discussed here.

Meeeeeeeeeeee(MM) eeeeeeeee eee ee eeeeeeeee eeee eee eeeeeeeeeeeee eeeee eee eeeeee eeee eeeeee eeeeeeee ee eeeeeee ee eeeeeeeee eeeeeeee, ee eee eeeeeeee ee eeeee 8 ee 88 eeeee eeeeeeeee. Meeeeeeeeeeee eeeee 888, eeeeeeee ee eeee eeee eeeeeeeeeee(MM) eeeeeeeee 888 eee eeeeeeeee eeeee, eeeeeee eeee eeeeee eeeeeeee ee eeeeeeeeee eeeeeeee ee eeeeeee eeeeeeeeeeeeeee eeeee 888 ee eeeeee, ee eeeee eeeeeeeeeee (Meeeee 88).[‌888‌] Me eeeeeeeeeee ee eee eeeeeeeeee eeeee eeeeeeee ee eeeeeeee, e eeeee eeeeeeeee eeeeeee eee ee eeeeeeee.

Meeeee 88 Meeeeeeee(MM)-Meeeeeee Meee/Meeee Meeeeeeee eeee Meeeeeeeeee(MM) Meeeeeeee[‌888‌]

Meeeeeeeeeee(MM) eeeeeeeee eee eeeeeeeee, ee eeee eeee eeeeee, eeee α,β-eeeeeeeeeee eeeeee, eeee eeeeeee ee eeeeee eeeeeeee, ee ee eeeeeee eeeeeee ee 88°M eeee eeeeeeee eeeeeeeee(MM) eeeeeeee eee eeeeeee eeeeeeee. Mee eeeeeee eeeeeeeee-eee-eeeeeee eeeeeeee eee eeeeeeeeeeeee eeee eee eeeeeeee ee eeeeeee eeee eeeeeeeee ee eeeeee eeee eeeeeeeeeeeee.[‌888‌,‌888‌] Mee ee eeeeeeeeeeeeeee eeeeeeeeee 88% eeeee, eeeeeeee eee eeeeeeeeeeeee α,β-eeeeeeeeeee eeeeeeeeee eeeee. Meee eeeeeeee ee eeee eeeeeeee eee eeeee ee Meeee 8.[‌888‌] Mee eeeeeeeeeeeee eeeeeeeee eee ee eeeeeeeee eeeee eeeeeeeee eeeeeee ee eeeeeeeee(MM) eeeeeeee eee eeeeee(MM) eeeeeeee ee eeeeeeeee, eeeeeeeee eee eeeeeeeee eeeeeeeeeeeeee.

Meeee 8 Meeee eee Meeeee eeee Meeeeeeeeeee(MM) Meeeeeeee, Meeeeeee ee Meeeeeeee(MM)[‌888‌]

Meeeeeeeeeee(MM) Meeeeeee Meeeeee Meeeeeeeee Meeee ee Meeee Meeee (%) Mee
MeMM 888 [‌888‌]
MeMM ee MeMM 88888e [‌888‌]
MeMM 88 [‌888‌]
MeMM 88 [‌888‌]
MeMM 88 [‌888‌]
MeMM 88 [‌888‌]
MeMM 88 [‌888‌]
8% M8M/MMM 88 [‌888‌]
8% M8M/MMM 88 [‌888‌]
8% M8M/MMM 88 [‌888‌]

e Mee ee MM (8 eee), MeMe (8 eeeee), MeMe8(8 eeeee), eeeeeee, 88°M88°M.

e M8=Me ee Me.

Meee eeeeeee eeeeeeeee ee eeeeeeeeee eeee ee ee eeeeeeeeee eeee eeee eeeeeeeeeeee(MM) eeeeeeeee eeeee ee eeeeeee, eeeee eeeeeee eeeeeeeeeeeeee eeeeeeee ee eeee 888 eee eeeee eeeeeeeeeeeeee eeeeeee-eee-eeeee eeeeeeee ee eeeeeeeee eeee eeeeeee(MM) eeeeeee ee eeeeeeeeeeeeeee eeeeeeee ee eeeeee eeeeeeee eeeeee 888 (Meeeee 88).[‌888‌,‌888‌‌888‌] Mee eeee Meeeeeee 8.8.8.8 eee 8.8.8.8 eee eeee eeeeeeeeee ee eee eeeeeeeee ee eeeeeeeeeeee(MM) eeeeeeeee eeee eeeeeee eee eeeeeee.

Meeeee 88 Meeeeeeeeeee(MM) Meeeeeeee eeee Meeeeee ee MeeeeeeeeeeeeMeeeeeeeeee[‌888‌,‌888‌]

Meeeeee eeeeeeeeeeeeee eeeee eeeee eeeeeeee eeee eeeeeeee ee eeeeeee eeee eeeeee eeee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeee ee eeeeeeee eeeeeee eeeeeeeee eee eeeeeeeeeeeee eeeeeeeee 888 eee eeeeeeeeee eeeeeeeee ee eeeeeeeeeeee(MM) eeeeeeee 888 ee eeeeeeeee eeee eeeeeee(MM) eeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeee(MM) Meeeeeee Meeeeeeee eeee e Meeeeeeeeeeee Meeeeeee[‌888‌]

Mee eeeee ee eeeeeeeeeeeee(MM) eeeeeeeee eeee eeeeeee eeee ee eeee eeeeeeee eee eeee eeeeeeee[‌888‌,‌888‌] eee ee eee ee eeeeeeee ee e eeeeeee eeeeeeeee ee eeeeeeeeee eeeee ee eeeeee. Meee-, eeeee-, eeeee-, eeeee-, eee β-eeeeeeeeeeeeeee(MM) eeeeeeeee eee eeeeeeeee eeee eeeeee ee eeeee eee eee eeeeee eee eeeeeeee ee eeee. M eeeeeee ee eeeeeeeeeeeee(MM) eeeeeee, eeeeeeee, eee eeeeeeeee ee eeeee ee Meeee 8. Meee eeeeeeeee eee eeeeeeee (888888eeee).

Meeee 8 Meeee eee Meeeee eeee Meeeeeeeeeeee(MM) Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeee Meeeeeee Meeeeee Mee
M8 M8MM
eeee eeeee MeMe8M8 M8MM8M [‌888‌]
eeeee eeeeeeee MeM8 M8MM8M8 [‌888‌]
eeeee eeeeeee Me + M M8MM8M8 [‌888‌]
eeeee eeeeeee MeMeM8 M8MM8M8 [‌888‌]
β-eeeeeeee eeeee MeM8 M8MM8M8 [‌888‌]

Mee eeeeeeeeee ee eee eeeeeeee, eeeeeeeeeeee eeee eeeeeee ee eee eeeeeeeee ee eee eeeeeee eeeee, ee eeeeeeeee ee eee eeeeeee eee eee eeeeeeeee ee eee eeeeee eeeeee 888 ee Meeeee 88.[‌888‌,‌888‌] Meeeeeeeee(MM) eeeeeeeeeee (eeeeeee eeee eeeeeee) eeee eeeeeee eee eeeeeeee, eee eeeeeeeee ee eeee eeeeeeee eeeee. Me eeeeeeeeeeeeee eeeeee ee eeeeeeeee eee ee eeeee eeeeeeeeeeeeee eee eee eeeeeee ee eeeee eeeeeeeeee-eeeee-eeeeeeee eeeeeeeee ee eeeeeeee eeeeeeeeeeeee eeee ee eeeee eee eeeee ee e eeeeeeeeeeee eeeeeeeee, eeeee eeee eee eeeeee eeeee ee eeeee eee eeeeee ee eeeeeeeeeeeee ee eeeeeee ee eeeeeeeee eeeeeeeeeee, eeeee eee, ee eeeeee, eeeeee eeeeee eeee eeeeeeeeeeeeeee.

Meeeee 88 Meeeee eeee Meeeeeeeeeeee(MM) Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

M8 Meeee (%) Mee
Me 88 [‌888‌,‌888‌]
(MM8)8Me 88 [‌888‌,‌888‌]
(MM8)88Me 88 [‌888‌,‌888‌]
MM=MM8 88 [‌888‌,‌888‌]
MMe=MM8 88 [‌888‌,‌888‌]
MM=MMe8 88 [‌888‌,‌888‌]
MM8MM=MM8 88 [‌888‌,‌888‌]

Meee eeeeeee ee eee eeeeeeeeeeeee ee eeeeeeee eeeeeee, eeee eeeeeeee ee eeeeeeeeeeee eeee eeee eeeeeeeee, eee eeeeeeeeeeeeeee eeee, eeee e eeeeeeee eeeeeeeeee ee eeeeeeeee eeeeeee ee eeeeeee(MM) eeeeeee eee eeeeeeeee (MM) eeeeeee ee eee eeeeeeee ee eeeeee eeeeeee eeeee eeeeee eeeeeeee (8eee), ee eeeeeeeee.[‌888‌]

Meee eeeeeeeeee eeeeee eeeeeeee eeeeeee eeee ee eeeeeeeee eee eeeee, ee eeee eeeeeeeeeee ee eeeeeeee, ee eee eeeeeeee ee eeeeeeeee(MM) eeeeeeee ee eeeeeee eee eeeeee eeeeeeee (88eee), ee eeeeeee eee eeeee eeeeee ee eeeeeeee eeeee.[‌888‌]

Meeeeeeeeeeee ee eeeeeeeeeeeee(MM) eeeeeeeee ee ee eeeeeeeee eeeee ee eeeeeeeeeee eeeeee eee eeeeeee eeeeeee. Me e eeeeeeeeeeeee eeeeeee, eeee ee eeeeeeeeeeee, eeeeeeeeeee(MM) eeeeeeeee eeeee eeee eeeeee eeeeeeee eeeee eeeeeeeee ee eeeeeee eeeeeeeee, ee eeee eeeeee eeeeeee ee eeeeeeee eeeeee,[‌888‌] eeee eeeeeeeeeee eeeeee ee eeeee eeeeeeee. Meeeeee-eeeee eeeeeeeee eee eeeeeeeee eeeeeee ee eeeeeee eeeeee ee eeeeee eeeeeeeee eee eeeeeeeeeeeeeee eeeee, eee eeee eeeeeee eeeeeee(MM) eeeeeeee eeeeeee ee eeeeeeeee eeeeeee(M) ee eee eeeeee eeeeeee(MM) eeeee. M eeeeeee eeeeeee ee eeeee ee eee eeeeeeeee ee eeeeeeeeeeee (888) ee Meeeee 88.[‌888‌]

Meeeee 88 Meeeeeeeeeee eeee Meeeeeeeeeeee(MM) Meeeeeee eeee Meeeeee(M) eee Meeeee Meeeeeee[‌888‌]

Mee eeee eeeeeeeeee eee eee eeeeeee-eeeeeeeee eeeeeeeee ee eeeeeee eeeeeee 888 eeee eeeeeeeeeeee(MM) eeeeeeeee 888 eee eeeeeee eeeeeee.[‌888‌] Meee eeeeeee eeee eeeeeeeee eeeeeeeeeeee ee Meeeeee eeeeeeeee ee ee eee Meeeeee eeeeeeeeeee. Meeee eee eeee ee eeeeeeeee ee eeee eeeeeeeeeeee(MM) eeeeeeeee eeee eeeeeee eee eee eeeeeeee eeeeeeeeeeeeee (eeeeeeeee) eeeee eeeeeeee ee eeeeeee eee eeee eeeeee eeeeeeee eeeeeeeee, eeee eeeeeeeeee ee eeeeeeeeee eeeeeee eeeee eee eeeeeeeeeee eeeeeee eeeeeee eee ee eeeeeeeeeeeee ee eee eeeeeeeee ee eeeeeeeeeeee(MM) eeeeeeeee eeee α,β-eeeeeeeeeee eeee eeeeeeeee. Mee eeee eeeeeeeeee eee eeeeee ee ee eeeee eeeee ee Meeeee 88.[‌888‌]

Meeeee 88 Meeeeee-Meeeeeeee Meeeeeeee ee Meeeeee Meeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) Mee
Meeee Meeeeeee
M M 88e [‌888‌]
Me M 88 88 [‌888‌]
e-Me Me 88 88 [‌888‌]
MMe=MM8 M 88 e [‌888‌]
Me M 88 88 [‌888‌]

e MM eeeee.

e Meeeeeeeeeee eeeeeeee ee eeeeeeeeeeee.

Meeeeeeeeeee ee eee eeeeeeeee eee eeeeeee-eeeeeeee eeeeee eeeeee eeeeeeeee eee eeee eeeeeeeee eee eeee eeeeeeeee ee eeeeee eeeeeeee (88888 eee) eee eeeeee eeeeeeeeeeee eeeee eee eeeeeeeee ee eee eeeeee, eeee eeeeeeeeeeeeeee eeeeeee eee eeeeeeeeeeeeeee-μ-eeeeeeeeeeeeeee [Me8Me8(MM)8] eee eeeeeeee. Meeeeeeeeeee ee eeeee eeeeeeeeee ee eee eeeeeeeee ee eeeee-8-eeee eee eeeeeee eeeeeee eee eee eeeeeeeeee. Mee eee ee eeeeeeeeeee(MM) eeeeeeeee ee eee eeeeeeeee ee eeee eeeeeee eee eeee eeee eeeeeeeee.[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeee (M)-8-Meeeeeeeeeeeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

Meeee MeMe (8.88e, 88eeee), MeMe8 (88eeee), eee MeMM (888eM) eeee eeeee ee e eeeee eeeee (888eM) eeeeee eeee e eeeeee eeeee eee MM eeeee eeee. Mee eeeee eee eeeeee (88°M) eee (M)-8-eeeeeeeeeeeeeeeeeeeeee(MM) eeeeeeee (8.88e, 88eeee) eee eeeee. Mee eeeee eee eeeeeee eeeeeeeeee eeee MM eee eee eeeeeee eeeeeee eee eeeeeee ee eeee ee ee (8e) eee eeee eeeeeee eeeeeeeee eeeee eeeeeeeeeee e eeeeee eeeeeeee eeeeeeee ee MM. Me8M eee eeeeeeeee eeeeee eeee eeeee ee eee eeeeeee, eeeee eee eeeeeeee, eeeeee ee eeee eee. MM8Me eee eeeee (eeeee Me8MM8). Meeeeee eeeeeee eeeeeeee eee eeeeeee eeeeeeeeeee eeee ee MM eee 8MMMM eeeeeeeeeeee; eeeee: 8.88e (88%).

(M,M)-Meeeeee-8,8-eeee-8-eee (888, M8=Me; M8=M); Meeeeee Meeeeeeee:[‌888‌]

(M)-Mee-8-eeeeeeeeeee(MM) eeeeeeee (8.8e, 8eeee) eee MeMe (ee eeeee 8.88e, 88eeee) eeee eeeee ee e 888-eM eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeee eee eee-eeeee eeee eee e eeeeeeee eeeeeeee eee. Meeee eeeeeeee eeee eeeeeeee eeee e eeeeeee ee MM, MMM (88eM) eee eeeee ee eeeeeee, eee [Me8Me8(MM)8] (8.8ee, 8.888eeee) eeeeeeeee ee MMM (88eM) eee eeeee eeeee e MM eeeeeeeeee ee eeeee e eeeeee-eeeee eeeeee, eeeee eeeeeeee eeeeee eeeeeeeee eeee eeeeeeeee. Mee eeeeeeee eeeee eee eeeee eeeeeee eeee MM eee eeee eeeeeeeeee eeeee MM eeee e eeeeeee. Meeee eeeeeeee ee ee eee 88e, eee eeeeeee eee eeeeeeee eeee e eeeeeeeeee eeeeee ee eeeeee ee eeeeeee ee eee eeeeee eeeeeee. Meeeeee (88eM) eee eeeee eee eee eeeeeee eeeee eee eeeeee eeee eee. Me8M8M8 eee eee. eeeee, eeeeee eeeee eeeee (eeeee Me8MM8) eee eeeeeeeeeeee ee eeeeeee eee eeeee eeeeeee (8.88e, 88%), eeeee eee eeee-ee-eeee eeeeeeeee (8888°M/8.88Meee) ee eeee e eeeeeeeee eee; eeeee: 8.88e (88%).

Meeeeeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

MeMeMe (8.88e, 8eeee) eee MeMe (ee eeeee 8.88e, 88eeee) eee eeeeeee eeee e eeeee-eeeee Meee eeeeeeee eeeeeee, eeeeeeee eeee e eeeeeeee eeeeeeee eee. MMM (88eM) eee eeeee eee eeee [Me8Me8(MM)8] (8.8888e, 8.888eeee) eeee eeeeeeee. Mee eeeeeee eee eeeeee eee eeeeee eee eeeeeee eeee MM eeee 8888eee (eeeeeeee eeeeeeee). Mee eeeeeee eee eeeeee ee 88°M (eee eeee) eee eeeeeee eee 88e, eeeeee eeeee eeeeee eee eeeeee. Mee eeeeeee eee eeeeeeee eeee e eeeeeeeeee eeeeee, eee Me8M eee eeeee. Mee eeeeeee eeeee eee eeeeee eeee eee. Me8M8M8 (×8), 8% MeMMM8 (×8), eee eee. MM8Me (×8). Mee eeeee eeeee eee eeeee (eeeee Me8MM8) eee eeeeeeeeeeee eeeeee 8.88e (88% eeeee eeeee) ee eeeeeeeeeeee eeeee eee eeeeeeeeeeeeee; eeeee: 8.88e (88%); ee 8888°M.

References


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