Borinic Acid‐Catalyzed Regioselective Ring‐Opening of 3, 4‐ and 2, 3‐Epoxy Alcohols with Halides. Issue 2 (17th December 2019)

• Record Type: Journal Article
• Authors: Wang, Grace; Taylor, Mark S.
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 2(2020)
• Page Start: 398
• Page End: 403
• Publication Date: 2019-12-17
• Subjects: boron -- halides -- homogeneous catalysis -- regioselectivity.; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201901268
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Methods for the regioselective ring‐opening of 3, 4‐epoxy alcohols and 2, 3‐epoxy alcohols with halide nucleophiles, using a diarylborinic acid catalyst, are disclosed. Ring‐opening occurs at the position proximal to the OH group, an effect ascribed to a catalytic tethering mechanism whereby coordination to the substrate OH group positions the diarylborinic acid to deliver a coordinated halide nucleophile. These methods provide access to halohydrin substitution patterns that were not previously accessible through catalytic epoxide ring‐opening reactions. Abstract :