- Cobalt-Catalyzed Carbocyclization of o-Iodobenzaldehydes and o-Iodophenylketones with Alkynes
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(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.
- Chang, Kuo-Jui,Rayabarapu, Dinesh Kumar,Cheng, Chien-Hong
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- Synthesis of Indanones and Spiroindanones by Diastereoselective Annulation Based on a Hydrogen Autotransfer Strategy
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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.
- Chen, Yate,Ding, Zhengtian,Wang, Yiming,Liu, Wenfeng,Kong, Wangqing
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supporting information
p. 5273 - 5278
(2021/02/03)
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- Cobalt-catalyzed regioselective [3+2] annulation of ortho-formyl and acetyl substituted phenylboronic acids with alkynes
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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
- Ueda, Mitsuhiro,Ueno, Tamami,Suyama, Yuki,Ryu, Ilhyong
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supporting information
p. 2972 - 2974
(2017/07/11)
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- Palladium-catalyzed annulation of alkynes with ortho -halide-containing benzyl alcohols in aqueous medium
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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.
- Feng, Jie,Lu, Guoping,Lv, Meifang,Cai, Chun
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p. 10561 - 10567
(2015/02/19)
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- Palladium(O)-catalyzed regioselective and multicomponent synthesis of 1,2,3-trisubstituted 1H-indenes
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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.
- Tsukamoto, Hirokazu,Ueno, Tatsuhiko,Kondo, Yoshinori
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p. 3033 - 3036
(2008/02/09)
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- Rhodium-catalyzed synthesis of indenols by regioselective coupling of alkynes with ortho-carbonylated arylboronic acids
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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
- Shintani, Ryo,Okamoto, Kazuhiro,Hayashi, Tamio
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p. 1294 - 1295
(2007/10/03)
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- Synthesis of 1H-inden-1-ol derivatives via rhodium-catalyzed annulation of o-acylphenylboronic acids with alkynes
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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
- Matsuda, Takanori,Makino, Masaomi,Murakami, Masahiro
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p. 1416 - 1417
(2007/10/03)
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- Cobalt-catalyzed regioselective carbocyclization reaction of o-iodophenyl ketones and aldehydes with alkynes, acrylates, and acrylonitrile: A facile route to indenols and indenes
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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.
- Chang, Kuo-Jui,Rayabarapu, Dinesh Kumar,Cheng, Chien-Hong
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p. 4781 - 4787
(2007/10/03)
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