A Novel Regiospecific Synthesis of 1-Chloro-2-arylcyclohexenes

Abstract

An efficient high yielding chemoselective synthesis of eleven novel 1-chloro-2-arylcyclohexenes employing the Suzuki cross coupling of 1-bromo-2-chlorocyclohexene with eleven different aryl boronic acids and Pd(dppf)Cl2·CH2Cl2 catalyst is reported.

Synthesis of Vinyl Chlorides via Triphosgene–Pyridine Activation of Ketones

“…16 Ketone 5a (208 µL, 2.00 mmol) was dissolved in CH 2 Cl 2 (10.0 mL) along with triphosgene (593 mg, 2.00 mmol) and pyridine (647 µL 18 Ketone 5d (261 mg, 1.50 mmol) was dissolved in CH 2 Cl 2 (7.5 mL) along with triphosgene (445 mg, 1.50 mmol) and pyridine (485 µL, 6.00 mmol). After aqueous workup, the crude mixture was purified with column chromatography on silica gel, buffered with 1% Et 3 N, using 100% hexanes to afford vinyl chloride 6d ( …”

“…GC-MS: t R = 17.37 min; M + calcd for C 12 H 13 Cl,192.1;found,192.1. 2-Phenyl-1-chloro-cyclohexene (6d). 18 Ketone 5d (261 mg, 1.50 mmol) was dissolved in CH 2 Cl 2 (7.5 mL) along with triphosgene (445 mg, 1.50 mmol) and pyridine (485 μL, 6.00 mmol). After aqueous workup, the crude mixture was purified with column chromatography on silica gel, buffered with 1% Et 3 N, using 100% hexanes to afford vinyl chloride 6d (121 mg, 0.63 mmol) as a colorless oil.…”