Gold-Catalyzed Cyclizations of 4-Alkyl-2-yn-1-yl (Oxy)cyclohexa-2,5-dien-1-ones ( 1 ) to Develop Two Cyclizations via π-Alkyne versus π-Allene Activations

Organic Letters 2026 Open access

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Authors: Akshay Suresh Kshirsagar, Pei-Qin Liao, Tzuhsiung Yang, Rai-Shung Liu
DOI: 10.1021/acs.orglett.5c05132
Cited by: 1
References: 29

Abstract

High Resolution Image Download MS PowerPoint Slide This work reports two new gold-catalyzed cyclizations of 4-alkyl-2-yn-1-yl (oxy)cyclohexa-2,5-dien-1-ones ( 1 ) via gold−π-allene versus gold−π-alkyne routes, The π-allene route involves a [3.3] Claisen rearrangement of 1-alloxyallene intermediates to enable a 1,3-group migration, ultimately affording 2-substituted 3-formylbenzofurans ( 2 ). Density functional theory (DFT) calculations support this proposed mechanism in which water plays a key role. An alternative π-alkyne route contains cocatalyst PhNH 2 (10 mol %), leading to the formation of C 3,4 -fused tetrahydrobenzofuran-5(4 H )-ones ( 3 ) stereoselectively.

Fields of Study & Subjects

Catalytic Alkyne Reactions Sulfur-Based Synthesis Techniques Cyclization and Aryne Chemistry

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
3
Pages
1048–1053
Publication date
13 January 2026
Language
EN