Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
9.9.4.1.9 Method 9: Introduction of Aryl Groups

DOI: 10.1055/sos-SD-009-00244

König, B.Science of Synthesis, (20019246.

As an alternative to transition-metal-catalyzed coupling procedures of halo- or metallofurans, such as the Suzuki coupling (Section 9.9.4.2.6), aryl groups can be introduced to furans by reaction with arenediazonium salts.[‌529‌‌531‌] The two most important procedures are the Gomberg reaction and the Meerwein reaction. In the Gomberg method, arenediazonium salts are allowed to react with furan (1) in alkaline solution (pH 89).[‌532‌] Yields of aryl-substituted products, such as 303, between 20 and 40% are independent of the arylation agent (Scheme 97). This method has been used mostly for furan itself, where the α-positions are substituted with high preference.[‌533‌] Higher yields are reported for procedures in which a zinc(II) chloride stabilized diazonium salt reacts in furan as solvent.[‌534‌]

Meeeee 88 Meeeeeeee ee Meeeeeeeee eeee Mee Meeeeeeee (Meeeeee Meeeeeee)[‌888‌]

Meeeeeeeeee 88

Me8 Meeee (%) ee 888 Mee
Me 88 [‌888‌]
8-Mee 88 [‌888‌]
8-MeM8M8 88 [‌888‌]
8-MeMM8M8 88 [‌888‌]

Mee eeeeeeeee ee eeeeeeeeeee eeeeee eee Meeeeeee eeeeee ee eeee eeeeeeee. Me eeee eeeeeeeee eee eeeeeeeee eeee ee eeeeeee eeee eeeeee 888 ee eee eeeeeeee ee eeeeee(MM) eeeee ee ee eeeeee eeeee/eeeeeee eeeeeee ee eeeee eeeeee 888 (Meeeee 88).[‌888‌‌888‌] Meeeeeeeeeee ee eee eeeeeeeee eeee eee eee eM ee eee eeeeeee eeeeeeeee eee eeeee: eeeeeeeee eeeee eeee eeeeeeee-eeeeeeee eeeeee eeee eee eeee eeeeee ee eM 88, eeeeeee eeeeeeeee eeeee eeee eeeeeeee-eeeeeeeeeee eeeeeeeeeeee eeeeee ee eeeeeee ee eM 88.[‌888‌] 8-Meeeeeeeeee eeeeee eeeee, ee eeeeeeee, ee eee eeeee α-eeeeeeee (M8). 8-Meeeeee-eeeeeeeeeee eeeeee eeeee eeeee eeeee eeeeeeeeee eeeeeeeeeeeeee ee M8, eee eeeeee eee eee. Meeeeeeee eeeee eee ee eeeeeeee ee Meeeeeee eeeeeeeee ee 8,8-eeeeeeeeeeeeeee 888, eeeee eeeee eeee eeeeee ee eeee eeee-eeeeeeeeeee eeeeee 888 eeeee eeee eeee eeeeeeeeee (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeeeee ee Meeeeeeeee eeee Mee Meeeeeeee (Meeeeeee Meeeeeee)[‌888‌‌888‌]

Meeeeeeeeee 88

M8 Me8 Meeee (%) ee 888 Mee
8-MM8M Me 88 [‌888‌]
8-MM8M 8-Mee 88 [‌888‌]
8-MM8M 8-MeeMM 88 [‌888‌]
8-MM8M 8-MMM8M8 88 [‌888‌]
8-MM8M 8-MeM8M8 88 [‌888‌]
8-MM8M 8-M8MM8M8 88 [‌888‌]
8-MMM Me 88 [‌888‌]
8-MMM 8-Mee 88 [‌888‌]
8-MMM 8-Mee 88 [‌888‌]
8-MMM 8-eeeeeeee 88 [‌888‌]
8-MM8M Me 88 [‌888‌]
8-MM8M 8-MeMM8M8 88 [‌888‌]
8-MM8M 8-M8MM8M8 88 [‌888‌]

Meeeee 88 Meeeeeeee ee Meeeeeeeee eeee 8,8-Meeeeeeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

Me8 Meeee (%) ee 888 Mee
Me 88 [‌888‌]
8-MeeMM8 88 [‌888‌]
8-MeM8M8 88 [‌888‌]
8-M8MM8M8 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee Meeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee eeeeeeeee (8.8eee) ee eeeee MMe (88eM) eee M8M (88eM) eee eeeee e eeee ee MeMM8 (8.8e, 8.8eee) ee M8M (88eM) eee eee eeeeeee eee eeeeeee eee 88eee, eeeeeeeeeee e eeeeeeeeeee eeeee 8°M. MeMe8 (88.8e, 8.8eee) eee eeeee ee M8M (88eM) eee eeeee 88eee ee 8°M eee eeeeeeeeee eeeeeeeee eeee eeeeeee ee eeeeeeeeeee. MeMe eee eeeee ee eeeeeeee eeeeeeeeeeeee eee eee eeeeeeeee eeee eee eeeeeeeee ee eeeeeeeeee eee eeeee ee eeeee. Me e eeeeeeeeee eeeeeee eeeeeeeeee ee eee eeeeeeeeee eeeeeeeee eeee (8.8eee) ee eeeee (888eM) eee eeeee MeMM (8e, 88eeee) eee eee MeMMe (88e, 888eeee). Mee eeeeeee eee eeee ee 88°M eee 8e, eeeeeee eee 88e eee eeee eeeeee ee ee eeeee eeeeeeeeeeee. Mee eeeee eeeeeeee eeeeeeeee eeeeee eeeee, eee eeeeee eeeeeeee (8888eM) eee eeeeeeeee eeee Me8M, eee eeeeeee eeeee eee eeeeeeeeeeee eee eee eeeee eeeeeeee eeee eeeeeeee ee eeeeeeeeeeee ee eeeeeeeeeeeeee (MeMM/M8M 8:8) ee eeeee eee 8-eeeeeeeeee.

Meeeeeee Meeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

Me e eeee (8°M) eeee ee eeeeeeeee (8.8eee) ee 88% MMe (88eM) eee eeeee 88% ee MeMM8 (88eM) eee eee eeeeeee eee eeeeeee eee 88eee. 8-Meeeee eeee (88.8e, 8.8eee) ee eeeeeee (88eM) eee MeMe8·8M8M (8.8e, 88eeee) ee M8M (88eM) eeee eeeee eee eee eeeeeee eee eeee ee 88°M eee 8 e. Mee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeeeeee ee 8% ee MeMMM8 eeee, eee eee eeee eee eeeeeeee eeee eeeeeeeee. Meeeeeeeeee eeeeeeee eeee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeeeeeee. Meee eeee eeeeeeeee eeee MMMe8.

8-Meeeeeeeeee (888, Me=Me) ee Meeeeeee ee Meeee eeee 8,8-Meeeeeeeeeeeeee;
Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8,8-eeeeeeeeeeeeeeee (8.88e, 88eeee), eeeeeeeee eeeeeee (8eM, 88eee), eee eeeee (88eM, 8.88eee) eee eeee ee 88°M eee 88e. Mee eeee eee eeeeee eeee M8M, eee eeeeeee eeeee eee eeeee (Me8MM8), eee eeeeeee eeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeee ee eeee 8-eeeeeeeeeee; eeeee: 8.8e (88%); ee 8888°M/888Me.

References


Cookie-Einstellungen