53347-50-5

Upstream product

• 1801-42-9 2,3-diphenyl-1H-inden-1-one 
• 26260-02-6 2-iodobenzaldehyde 
• 501-65-5 diphenyl acetylene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 18982-54-2 o-bromobenzyl alcohol 
• 5159-41-1 2-iodobenzyl alcohol 
• 5324-00-5 2,3-diphenyl-1H-indene 
• 59046-72-9 o-(phenylethynyl)benzaldehyde 
• 98-80-6 phenylboronic acid 
• 40138-16-7 2-formylbenzene boronic acid 
• 4023-85-2 1-chloro-2,3-diphenyl-1H-indene 

Downstream Products

• 4023-85-2 1-chloro-2,3-diphenyl-1H-indene 
• 7474-64-8 (2RS,3RS)-2-phenyl-3-phenyl-2,3-dihydro-1H-inden-1-one 
• 1801-42-9 2,3-diphenyl-1H-inden-1-one 
• 53347-51-6 1-bromo-2,3-diphenyl-1H-indene 

Relevant academic research and scientific papers

Cobalt-Catalyzed Carbocyclization of o-Iodobenzaldehydes and o-Iodophenylketones with Alkynes

(Equation Presented) Treatment of various o-iodobenzaldehydes and o-iodophenyl ketones with alkynes in the presence of Co(dppe)l2 and Zn powder in acetonitrile at 80°C afforded the corresponding indenols in moderate to excellent yields with exceedingly high regioselectivity. For most unsymmetrical alkynes tested, the carbocyclization gave a single regioisomer.

Synthesis of Indanones and Spiroindanones by Diastereoselective Annulation Based on a Hydrogen Autotransfer Strategy

An unprecedented nickel-catalyzed domino reductive cyclization of alkynes and o-bromoaryl aldehydes is described. The reaction features broad substrate scope and is tolerant of a variety of functional groups, providing straightforward access to biologically significant indanones and spiroindanone pyrrolidine derivatives in good yields with excellent regio- and diastereoselectivity. Preliminary mechanistic studies have shown that indanones are formed by the cyclization of o-bromoaryl aldehydes and alkynes to form indenol intermediates, followed by hydrogen autotransfer.

Cobalt-catalyzed regioselective [3+2] annulation of ortho-formyl and acetyl substituted phenylboronic acids with alkynes

Treatment of alkynes with ortho-formyl and acetyl phenylboronic acids in the presence of a cobalt catalyst resulted in the formation of 2,3-disubstituted indenols in good yields. When aryl silyl alkynes were used, 2-aryl-3-silyl indenols were obtained reg

Palladium-catalyzed annulation of alkynes with ortho -halide-containing benzyl alcohols in aqueous medium

The Pd-catalyzed annulations of ortho-halide-containing benzyl alcohols with alkynes for the synthesis of indenones were achieved in aqueous Triton X-100 micelles with good yields and wide substrate scopes. Moreover, the indenones obtained in this procedure can be further functionalized to form some more synthetic useful derivatives via an environmental-friendly way.

Palladium(O)-catalyzed regioselective and multicomponent synthesis of 1,2,3-trisubstituted 1H-indenes

A multicomponent synthesis of biologically important indenes bearing three substituent groups at the 1-, 2-, and 3-positions from available o-ethynylbenzaldehyde derivatives and organoboron reagents under pailadium(O) catalysis is described. A two-component coupling reaction in methanol provides 1H-indenols, whereas a three-component reaction involving secondary aliphatic amines as the third component in DMF affords 1H-indenamines. This method allows combinatorial preparation of unsymmetrically substituted 1H-indenes that cannot be prepared via previous synthetic routes.

Rhodium-catalyzed synthesis of indenols by regioselective coupling of alkynes with ortho-carbonylated arylboronic acids

A rhodium/diene-catalyzed regioselective synthesis of indenols has been developed through the coupling of alkynes with ortho-carbonylated arylboronic acids. These reactions proceed under mild conditions in uniformly high yield and regioselectivity. The re

Synthesis of 1H-inden-1-ol derivatives via rhodium-catalyzed annulation of o-acylphenylboronic acids with alkynes

A rhodium-catalyzed annulation reaction of o-formyl-phenylboronic acid with alkynes occurred regioselectively at room temperature to give substituted 1H-inden-1-ol derivatives. o-Acetylphenylboronic acid also underwent the annulation reaction at 80°C to a

Cobalt-catalyzed regioselective carbocyclization reaction of o-iodophenyl ketones and aldehydes with alkynes, acrylates, and acrylonitrile: A facile route to indenols and indenes

An efficient cobalt-catalyzed carbocylization for the synthesis of indenols and indenes and a new method for reductive decyanation are described. 2-Iodophenyl ketones and aldehydes 1a-g undergo carbocyclization with various disubstituted alkynes 2a-k in the presence of Co(dppe)I2 and zinc powder in acetonitrile at 80 °C for 3 h to afford the corresponding indenol derivatives 3a-s and 4a-m in good to excellent yields. For some unsymmetrical alkynes, the carbocyclization was remarkably regioselective, affording a single regioisomer. The cobalt-catalyzed carbocyclization reaction was successfully extended to the synthesis of indene derivatives. Thus, the reaction of 2-iodophenyl ketones and aldehydes (1) with acrylates H2C=CHCO 2R (7a-d) and acrylonitrile H2C= CHCN (7e) proceeds smoothly in the presence of Co(dppe)Cl2/dppe and zinc powder in acetonitrile at 80 °C for 24 h to afford the corresponding indenes 8a-k and 9a-c in moderate to good yields. Interestingly, when 7e was employed for the carbocylization, reductive decyanation also occurred to give an indene derivative without the cyano functionality. A possible mechanism for this cobalt-catalyzed carbocyclization reaction is also proposed.