Sequential Cobalt/Rhodium‐Catalyzed Tandem Cyclization of Aromatic Aldehydes with Acrylates for Preparing 3‐Substituted Phthalides in Oxygen Atmosphere and Neat Water. Issue 2 (6th December 2021)

• Record Type: Journal Article
• Authors: Li, Xin‐Ran; Li, Wan‐Di; Wei, Wen‐Ting; Fan, Juan; Liu, Zhong‐Wen; Shi, Xian‐Ying
• Is Part Of: Asian journal of organic chemistry. Volume 11:Issue 2(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2021-12-06
• Subjects: Aromatic aldehyde -- Organic reaction in water -- Oxygen -- Phthalide -- Tandem cyclization; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100725
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Metal‐catalyzed C−H activation/tandem reactions of aromatic acids and functionalized alkenes is profound for constructing phthalide skeleton. However, most of these reactions employ stoichiometric amounts of metal additives and metal oxidants/toxic organic solvents. Herein, we describe a sequential cobalt/rhodium‐catalyzed tandem cyclization of aromatic aldehydes and acrylates for preparing 3‐substituted phthalides in one pot. This protocol features the use of water as a sustainable solvent and oxygen as the singular oxidant free of any additives. The use of aromatic aldehydes instead of aromatic acids as starting materials renders this route high atom economy, and the formation of water as a sole byproduct makes this process practical and environmentally benign. Abstract : A sequential cobalt/rhodium‐catalyzed tandem cyclization of aromatic aldehydes with acrylates for preparing 3‐substituted phthalides in one pot has been demonstrated. The reactions take place with renewable water as solvent and oxygen as the sole oxidant free of any additives, providing a useful insight for an environmentally friendly and sustainable access to 3‐substituted phthalides.