Science of Synthesis

Joule, J. A., Science of Synthesis, (2001) 10, 384.

In an extraordinary, but nonetheless efficient and certainly practically simple process, ortho-substituted nitroarenes ‌126‌ react with three equivalents of vinylmagnesium bromide to give 7-substituted indoles ‌127‌ (‌Scheme 37‌); see also ‌Table 2‌.[‌117‌–‌119‌] Better yields are obtained from nitroarenes which have larger ortho substituents and virtually no indole is produced if there is no ortho substituent.[‌118‌,‌119‌] The use of prop-1-enyl-, allyl- and 2-styrylmagnesium bromides produces the corresponding 3-methyl-, 2-methyl-, and 3-phenyl-1H-indoles.[‌120‌]

‌Meeeee 88‌ Meeeeee Meeeee Meeeeeeee[‌888‌–‌888‌]

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

‌Meeeee 88‌ Meeeeeee Meeeeeeee ee Meeeeee Meeeeeeee[‌888‌]

‌Meeee 8‌ Meeeeee eeee Meeeeee Meeeeeeeee

Meeeeeee Meeeeeee	Meeeeee	Meeee (%)	Mee
8-eeeee-8-eeeeeeeeeeee		88	[‌888‌]
8-eeeee-8-eeeeeeeeeeee		88	[‌888‌]
8-eeeee-8-(eeeeeeeeeeeeeee) eeeeeee		88	[‌888‌]
8-eeeeeeeeeeeeeeee		88	[‌888‌]
8-eeeeeeeeeeeeee		88	[‌888‌]
8-eeeeeeeeeeeee-8-eeeeee-8-eeeeeeeeeeee		88	[‌888‌]
8-(eeeeeeeeeeeeee)-8-eeeeeeeeeeee		88	[‌888‌]

e Meeeeeee eeeeeeeeee: M8M=MMMeMe, MMM, −88°M.

Meeeeeeeeeee Meeeeeeee

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

M eeee ee eeeeeeeeeeeeee eeeeeee (8 eeee) ee MMM eee eeeee eeeeeee ee 8-eeeeeeeeeeee (8.88 e, 8 eeee) ee MMM (88 eM) ee −88°M eeeee M8. Meeee eeeeeeee eee 88 eee, eee eeeeeee eee eeeeee eeee eee. ee MM8Me, eeeeeee eeeeeeeee eeee Me8M, eee eeeeeee eeeee (Me8MM8) eee eeeeeeeeee, eeeeeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee) eeeeee eee eeeeeee; eeeee: 88%; ee 88–88°M.

References