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10.1.4.1.4.1 Reactions of Halobenzo[b]furans

DOI: 10.1055/sos-SD-110-00529

Kwiecień, H.Science of Synthesis Knowledge Updates, (20144328.

3-Bromobenzo[b]furan (526) readily undergoes hydrodehalogenation on treatment with sodium borohydride and N,N,N′,N′-tetramethylethylenediamine as a hydride source in combination with a palladium catalyst at room temperature (Scheme 327).[‌567‌]

Meeeee 888 Meee-Meeeeeeeeee Meeeeeeeeeeeeeeeeee ee 8-Meeeeeeeee[e]eeeee[‌888‌]

Meeeeeeeeee 888

Meeeeeee Meeee ee MeMM8 eee MMMMM Meee (e) Meeee (%) Mee
Me(MMe)8 (8 eee%), Me8M (88 eee%) 8.8 88 88 [‌888‌]
MeMe8(eeee)•MM8Me8 (8 eee%) 8.8 8 88 [‌888‌]

8,8-Meeeeeeeeeee[e]eeeee (888) eeeeeeeee eeeeeee–eeeeeee eeeeeeee eeee eeeeeeeeeeee ee −88 °M eee eeeeeeeeeee eeee eeeee eeee eeeee 8-eeeeeeeeee[e]eeeee (888) ee 88% eeeee (Meeeee 888).[‌88‌] Meeeeeeee, 8-eeeeeeeeeee[e]eeeee (88) ee eeeeeeee eeee 8-eeee-8-eeeeeeeeeee[e]eeeee ee 88% eeeee ee eeeeeee–eeeeeee eeeeeeee eee eeeeeeeeeee eeee eeeeeee eeeeeeee eeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeee–Meeeeee Meeeeeee eee Meeeeeeeeee ee Meeeeeeeeee Meeee[e]eeeeee[‌88‌,‌888‌]

Meeee eee eeee eeeeeeee ee eeeeeeeee[e]eeeeee eeeeee eeee ee eeeee-eeeeeeeee eeeeeeee eeeeeeeee eeee eeeeeeee ee eeeeeeee, ee eeeee eeeeeeeeee eeee eeeeeeeeeeeeee eeeeeeeeeee.

Meeeeeeeeeee eeeeeeeeeeee ee eeeeeee ee eeeee[e]eeeeee eeeee eeeee eeeeee eeee ee eee eeeeeee ee eeeeeeeee ee e eeeeeeeeee eeeeeeee-eeeeeeeeeee eeeee; eee eeeeeee, eeeeeeeee ee 8-eeeeeeeeee[e]eeeee-8-eeeeeeeeeeee (888) eee 8-eeeeeeeeeee[e]eeeee-8-eeeeeeeeeeee (888) eeee eeeeee eeeeeeeeeeee eeee eee eeeeee eeeee ee eee eeeeeeee-eeeeeeeeeee eeeeeeeee 888 eee 888, eeeeeeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeeeeee Meeeeeeeeeee ee Meeeeee eeee Meeeee Meeeeeeeeeee[‌888‌]

8-Meeeeeeeeee[e]eeeee-8-eeeeeeeeeeee (888) eeeeee eeee eeeeee eeeee ee eee eeeeeeeeeee, eeeeeeee eeeeeeeeee eeeeee 8-eeeeeeeeee[e]eeeee-8-eeeeeeeeeeee (888). Meee eeeeeeee ee eeeeeee eeee eeeeeeee eeeeeee ee eee eeeeee 8-eeeeeeeeee[e]eeeee-8-eeeeeeeeeeee (888) (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee 8-Meeeeeeeee[e]eeeee-8-eeeeeeeeeeee eeee 8-Meeeeeeeeee[e]eeeee-8-eeeeeeeeeeee eee ee Meeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeee[e]eeeee (8); Meeeeee Meeeeeeee Meeee Meeeeeeee(MM) Meeeeee:[‌888‌]

Meeee MMM (88.8 eM) eee eeeeeeee eeeee eeeeeeee eeeee eee e eee eee, eeee Me(MMe)8 (8.8 ee, 8.888 eeee, 8 eee%) eee Me8M (88.8 ee, 8.888 eeee, 88 eee%) eeee eeeee, eee eee eeeeeeeee eeeeeee eee eeeeeee ee ee eee 88 eee. 8-Meeeeeeeee[e]eeeee (888; 8.888 e, 8.88 eeee), MMMMM (8.888 e, 8.88 eeee, 8.8 eeeee), eee eeeeeee MeMM8 (88.8 ee, 8.88 eeee, 8.8 eeeee) eeee eeeeeeeeee ee eeeeeeee. Mee eeeeeee eee eeeeeee ee ee ee eeeeee ee 88 °M eeeee eeeee eee 8 e. Mee eeeeeee eee eeeee ee ee eeeee eee eeeeeeeee eeee MeMMe. Mee eeeeeee eeeee eee eeeeeeeee eee eeeee, eee eeeeeee eee eeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeeeeee eeeee/MeMMe) ee eeee eee eeee eeeeeee; eeeee: 88 ee (88%).

Meeee[e]eeeee (8); Meeeeee Meeeeeeee Meeee [8,8′-Mee(eeeeeeeeeeeeeeeee)eeeeeeeee]eeeeeeeeeeeeeeeee(MM):[‌888‌]

M eeeeeee ee 8-eeeeeeeeee[e]eeeee (888; 8.888 e, 8.88 eeee) ee eeeee MMM (88.8 eM) eee eeeeeeee ee eeeeeeee eeeee eee e eee eee. Meee, MeMe8(eeee)•MM8Me8 (88.8 ee, 8.888 eeee, 8.8 eee%), MMMMM (8.888 e, 8.88 eeee, 8.8 eeeee), eee eeeeeee MeMM8 (88.8 ee, 8.88 eeee, 8.8 eeeee) eeee eeeeeeeeee ee eeeeeeee. Mee eeeeeee eee eeeeeee ee ee eeeee eeeee eee 8 e. Mee eeeeeee eee eeeee ee ee eeeee eee eeeeeeeee eeee MeMMe. Mee eeeeeee eeeee eee eeeeeeeee eee eeeee, eee eeeeeee eee eeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeeeeee eeeee/MeMMe) ee eeee eee eeee eeeeeee; eeeee: 88 ee (88%).

8-Meeeeeeeee[e]eeeee (888); Meeeeee Meeeeeeee:[‌88‌]

M 8.8 M eeee ee MeMe ee eeeeee (8.888 eee) eee eeeee ee e eeee ee 8,8-eeeeeeeeeeee[e]ee­eee (888; 88.8 e, 88 eeee) ee eeeee MMM (888 eM) ee −88 °M eeeee M8. Mee eeeeeee eee eeeeeee eee 88 eee, eeeeeee eeee MeMM (8 eM), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeee eeee M8M eee MM8Me8. Mee eeeeeee eeeee eee eeeeeeeee, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeeeee (eeeeee eee, eeeee­eeee eeeee) eeeeeeee eee eeee eeeeeee ee e eeeee; eeeee: 88 e (88%); ee 88 °M.

References


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