Studies of Reversible Conjugate Additions. Issue 23 (4th July 2013)

• Record Type: Journal Article
• Authors: Zhong, Ye; Xu, Yufang; Anslyn, Eric V.
• Is Part Of: European journal of organic chemistry. Issue 23(2013)
• Page Start: 5017
• Page End: 5021
• Publication Date: 2013-07-04
• Subjects: Sulfur -- Reversible reactions -- Michael addition -- Combinatorial chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300358
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Benzalcyanoacetamides were designed and synthesized as reversible thiol conjugate addition acceptors. These thia‐conjugate additions can rapidly and reversibly achieve equilibrium under aqueous conditions at neutral pH. Kinetic studies show that electron‐withdrawing groups at the 4‐position of the phenyl ring of the benzalcyanoacetamides promote the conjugate addition at equilibrium. Dynamic thiol exchange of these conjugate acceptors is faster than singly activated α, β‐unsaturated carbonyl compounds. These thia‐conjugate additions can be assembled as potentially useful components in dynamic combinatorial chemistry. Abstract : Benzalcyanoacetamides were studied with thiols as reversible thiol conjugate addition acceptors. These thia‐conjugate additions can rapidly and reversibly achieve equilibrium under aqueous conditions at neutral pH, which verifies the ultimate use of these conjugate acceptors in dynamic combinatorial chemistry.