Science of Synthesis

Amador, A. G.; Scholz, S. O.; Skubi, K. L.; Yoon, T. P., Science of Synthesis: Photocatalysis in Organic Synthesis, (2018) 1, 467.

Single-electron reduction of diiodomethane using tris(2,2′-bipyridyl)ruthenium(II) hexafluorophosphate {[Ru(bipy)3](PF6)2} leads to the generation of a radical carbenoid equivalent capable of reacting with a variety of electron-rich styrenes[‌8‌] and chalcones[‌9‌] ‌1‌ in a stereoconvergent manner to give exclusive formation of trans-cyclopropane products of type ‌2‌. A variety of 1,2-disubstituted E- or Z-(het)arylalkenes also undergo reaction in high yield, but electron-deficient styrenes give either low yield or no product (‌Table 1‌).

‌Meeee 8‌ Meeeee Meeeeeeeeeeeeeee eee Meeeeeeee Meeeeeeeeeeeee ee Meeeeeeeeeeee[‌8‌,‌8‌]

Meeee	Meeeeeeee	Meeeeee	Meeee (%)	Mee
8			88e	[‌8‌]
8			88	[‌8‌]
8			88	[‌8‌]
8			88	[‌8‌]
8			88	[‌8‌]
8			88	[‌8‌]
8			88	[‌8‌]
8			88	[‌8‌]
8			88	[‌8‌]
88			88	[‌8‌]

e 88% eeeee eee e eeee-eeeee eeeeeeee ee eee M-eeeeee.

Meeeeeeeeeee Meeeeeeee

eeeee-8-Meeeee-8-(8-eeeeeeeeeeeee)eeeeeeeeeeee (‌Meeee 8‌, Meeee 8); Meeeeee Meeeeeeee:[‌8‌]

M eeeeeeee eeeeee eee eeeeeee eeee [Me(eeee)8](MM8)8 (8.88 ee, 8 µeee, 8 eee%), MeMM (8 eM, 8.8 M), 8-(8-eeeeeeeeeeeee)eeee-8-eee [eeeee (M/M) 8:8; 88 ee, 8.8 eeee, 8 eeeee], 8.88 M ee Me8M8M8 (8.8 eM, 8.8 eeee, 8 eeeee), eMe8MMe (888 µM, 8.8 eeee, 8 eeeee), eee MM8M8 (88 µM, 8.8 eeee, 8.8 eeeee). Mee eeeeeee eee eeeeeeee ee eeeee eeeeee–eeee–eeee eeeeee eeeee eeeee, eee eeee eeeeeee ee ee eee eeeeeeeeee eeee eeeeeee eeeee eeee e eeeeeee eeeeeeeeeee eeeeeeeee (MMM, 88 M) ee e eeeeeeee ee 88 ee. Meeee 8 e, MM8M8 (88 µM, 8.8 eeee, 8.8 eeeee) eee Me8M8M8 (888 ee, 8.8 eeee) eeee eeeee eee eee eeeeeee eee eeeeeee eee eeeeeeeeee eee ee eeeeeeeeee 88 e. Mee eeeeeeee eee eeeeeeee eeee M8M (8 eM) eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee (eeeeee eee eeeeeeeeeee eeee eeeeee eeeeeee ee eeeeeee); eeeee: 88 ee (88%).

eeeee-8-Meeeee-8-(8-eeeeeeeeeeeee)eeeeeeeeeeee (‌Meeee 8‌, Meeee 8); Meeeeeee Meeeeeeee eee e Meee-Meeee Meeeeeee:[‌8‌]

M eeeee-eeeeeeee eeeee eee eeeeeee eeee [Me(eeee)8](MM8)8 (88 ee, 88 µeee, 8 eee%), MeMM (88 eM), (M)-8-(8-eeeeeeeeeeeee)eeee-8-eee (8.8 e, 8.88 eeee), 8.88 M ee Me8M8M8 (88 eM, 88.8 eeee, 8 eeeee), eMe8MMe (8.8 eM, 88.8 eeee, 8 eeeee), eee MM8M8 (8.88 eM, 88.8 eeee, 8.8 eeeee). Mee eeeeeee eee eeeeeeee ee eeeee eeeeee–eeee–eeee eeeeee eeeee eeeee eee eeeeee eeee ee eeeee eeeeeee. Meeee eeeeeeeeeee eeee e eeeeeee eeeeeeeeeee eeeeeeeee (MMM, 88 M) ee e eeeeeeee ee 88 ee eee 88 e ee ee, eee eeeeeeee eee eeeeeeee ee eeeeeeee ee M8M (888 eM) eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 888 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeeee); eeeee: 888 ee (88%).

References