Efficient Synthesis of 3-Iodoindenes via Lewis-Acid Catalyzed Friedel−Crafts Cyclization of Iodinated Allylic Alcohols

Zhou, Xiaobo; Zhang, Huimin; Xie, Xin; Li, Yanzhong

doi:10.1021/jo800232p

Cited by 57 publications

(23 citation statements)

References 43 publications

(18 reference statements)

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“…As the reaction occurs by an S N 1-type reaction, this method allows the selective protection of primary alcohols in the presence of secondary alcohols. [48] Catalytic amounts of BF 3 were used by Li and co-workers [49] in the catalyzed Friedel-Crafts intermolecular cyclization of iodinated allylic alcohol 30 (Figure 2). …”

Section: Boronmentioning

confidence: 99%

Direct Nucleophilic S_N1‐Type Reactions of Alcohols

et al. 2010

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In 2005, the ACS Green Chemistry Institute (GCI) and the global pharmaceutical corporations developed the ACS GCI Pharmaceutical Roundtable to encourage the development of green chemistry and green engineering in the pharmaceutical industry. The Roundtable has established a list of key research areas including the direct nucleophilic reactions of alcohols. The substitution of activated alcohols is a frequently used approach for the preparation of active pharmaceutical ingredients. Alcohols are transformed into the reactive halides or sulfonate esters, thereby allowing their reaction with nucleophiles. Although the direct nucleophilic substitution of an alcohol should be an attractive process, as one of the byproducts from the reaction yields water, hydroxide is a poor leaving group that hinders the reaction. Recently, the direct substitution of allylic, benzylic, and tertiary alcohols has been achieved through an SN1 reaction with catalytic amounts of Brønsted or Lewis acids. In this review, the approaches leading to a greener process are examined in detail, and the advances achieved to date in this important transformation are presented.

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Section: Boronmentioning

confidence: 99%

Direct Nucleophilic S_N1‐Type Reactions of Alcohols

et al. 2010

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“…23 56- 98 23 The intramolecular Friedel-Crafts allylic alkylation was shown by Li and co-workers to be an efficient strategy for the construction of indene derivatives (Table 1.3, entry 1). 24 By employing BF 3 •Et 2 O as the catalyst, the cyclization of a variety of allylic alcohols of the type 9 was reported to give the corresponding 3-iodo-1H-indene derivatives 11 (R 2 = I) in 55-90% yield under mild conditions, which are valuable compounds for constructing multi-aryl substituted indene derivatives through further Suzuki coupling reactions. 93 26 In the same year, Liu and co-workers described the preparation of highly substituted indenes and spiroindenes via intramolecular cyclization of arylated allylic alcohols 9 in the presence of TsOH•H 2 O (Table 1.3, entry 2).…”

Section: Allylic Alcoholsmentioning

confidence: 99%

Lewis and Br??nsted acid-catalyzed reactions of alcohol pro-electrophiles as novel synthetic strategies for C-X (X = C, N, O, S) bond formation

Zhang¹

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The work of this thesis has been directed toward establishing new Lewis and Brønsted acid-catalyzed reactions of alcohol pro-electrophiles as novel synthetic strategies for C−X (X = C, N, O, S) bond formation. This thesis is divided into three parts: Part I consists of Chapter I, which gives an introduction of Lewis and Brønsted acid catalyzed reactions of alcohol pro-electrophiles, particularly those containing a pendant activated alcohols such as allylic, propargylic, benzylic and cyclopropylmethyl functional group. Part II describes the new strategies developed for C−X (X = C, N, O, S) bond formation employing alcohols as pro-electrophiles. Chapter II reports iron(III) chloride catalyzed direct nucleophilic α-substitution of Morita-Baylis-Hillman alcohols with alcohols, arenes, 1,3-dicarbonyl compounds, and thiols. In Chapter III, a new method to indenols that relied on ytterbium(III) triflate catalyzed tandem Friedel-Crafts arylation/hydroarylation of propargylic alcohols with phenols is described. Chapter IV detailed the synthesis of highly substituted indene derivatives via Brønsted acid catalyzed intramolecular Friedel-Crafts cyclization of homoallylic alcohols. In Chapter V, a novel strategy to di-and trisubstituted thiazoles via Brønsted acid catalyzed cyclization of propargylic alcohols with thioamides was described. Chapter VI Chapter I. Alcohol Pro-electrophiles in Lewis and Brønsted Acid Catalysis

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“…The reaction also worked with FeCl 3 .6H 2 O, but the yield was low (71%) (entry 5). When other Lewis acids such as AlCl 3 , InCl 3 and TiCl 4 were employed, the product was obtained in lower yields (entries [6][7][8]. Switching the solvent to acetonitrile also lowered the yield (entry 9) while the reaction did not work in THF (entry 10).…”

Section: Halocyclization Of O-mentioning

confidence: 99%

Iron(iii) halide or iodine-promoted synthesis of 3-haloindene derivatives from o-alkynylarene chalcones

Akbar

Srinivasan

2015

RSC Adv.

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Efficient Synthesis of 3-Iodoindenes via Lewis-Acid Catalyzed Friedel−Crafts Cyclization of Iodinated Allylic Alcohols

Cited by 57 publications

References 43 publications

Direct Nucleophilic S_N1‐Type Reactions of Alcohols

Direct Nucleophilic S_N1‐Type Reactions of Alcohols

Lewis and Br??nsted acid-catalyzed reactions of alcohol pro-electrophiles as novel synthetic strategies for C-X (X = C, N, O, S) bond formation

Iron(iii) halide or iodine-promoted synthesis of 3-haloindene derivatives from o-alkynylarene chalcones

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Efficient Synthesis of 3-Iodoindenes via Lewis-Acid Catalyzed Friedel−Crafts Cyclization of Iodinated Allylic Alcohols

Cited by 57 publications

References 43 publications

Direct Nucleophilic SN1‐Type Reactions of Alcohols

Direct Nucleophilic SN1‐Type Reactions of Alcohols

Lewis and Br??nsted acid-catalyzed reactions of alcohol pro-electrophiles as novel synthetic strategies for C-X (X = C, N, O, S) bond formation

Iron(iii) halide or iodine-promoted synthesis of 3-haloindene derivatives from o-alkynylarene chalcones

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Direct Nucleophilic S_N1‐Type Reactions of Alcohols

Direct Nucleophilic S_N1‐Type Reactions of Alcohols