Modular Synthesis of Enantioenriched 1,1,2-Triarylethanes by an Enantioselective Arylboration and Cross-Coupling Sequence

Chen, Bin; Cao, Ping; Yin, Xiufeng; Liao, Yang; Jiang, Liyin; Ye, Jialin; Wang, Min; Liao, Jian

doi:10.1021/acscatal.7b00300

Cited by 138 publications

(42 citation statements)

References 82 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Subsequently, the Liao group developed an enantioselective Cu/Pd‐catalyzed borylative coupling of styrenes with aryl/alkenyl iodides by using a similar chiral SOP ligand . A series of enantioenriched 1,1‐diarylethyl and β‐arylhomoallylic boronates were easily prepared in high yields and with excellent enantioselectivities (Scheme ).…”

Section: Synergistic Cu‐b and Pd Catalysismentioning

confidence: 99%

Synergistic Pd/Cu Catalysis in Organic Synthesis

Huo

Zhang

2020

Chemistry A European J

120

View full text Add to dashboard Cite

Synergistic Pd/Cu catalysis has been utilized in the Sonogashira reaction since 1975. However, this strategy has not received much attention from the organic chemist community until recently. Synergistic Pd/Cu catalysis is becoming a proficient method for the development of catalytic reactions, including several new and efficient cross‐coupling reactions. Additionally, several challenging asymmetric reactions, including stereodivergent synthesis, have been discovered by the combined use of a chiral metal catalyst and a second achiral metal catalyst or two chiral metal catalysts. This review provides an overview of this field, with the aims of highlighting both the development of synergistic Pd/Cu catalysis in organic synthesis and the reaction mechanisms involved in this research area.

show abstract

Section: Synergistic Cu‐b and Pd Catalysismentioning

confidence: 99%

Synergistic Pd/Cu Catalysis in Organic Synthesis

Huo

Zhang

2020

Chemistry A European J

120

View full text Add to dashboard Cite

show abstract

“…[10] Over the last several years, our research group [11] and others [12,13] have developed methods for the arylboration of alkenes by Cu/Pd cooperative catalysis (Scheme 1B). In these reactions, an alkyl–copper intermediate is generated by catalytic borylcupration of an alkene, followed by palladium-catalyzed cross-coupling.…”

mentioning

confidence: 99%

“…[9] In recent years,copper-catalyzed carboboration reactions of alkenes have emerged as au seful strategy for chemical synthesis because the CÀBbond can be converted into other groups with ease,thus allowing for carbofunctionalization. [10] Over the last several years,o ur research group [11] and others [12,13] have developed methods for the arylboration of alkenes by Cu/Pd cooperative catalysis (Scheme 1B). In these reactions,a na lkyl-copper intermediate is generated by catalytic borylcupration of an alkene,f ollowed by palladium-catalyzed cross-coupling.T his strategy has been shown to be effective for the functionalization of alkenyl arenes,1,3dienes,v inyl silanes,and strained alkenes.…”

mentioning

confidence: 99%

Copper‐Catalyzed Borylacylation of Activated Alkenes with Acid Chlorides

2017

View full text Add to dashboard Cite

A method for the copper-catalyzed borylacylation of activated alkenes is presented. The reaction involves borylcupration of the alkene, followed by capture of the generated alkyl–copper intermediate with an acid chloride. The reactions operated with low catalyst loading and generally occurre within 15 min at room temperature for a range of activated alkenes. In the case of vinyl arenes, enantioselective borylacylation was possible.

show abstract

“…Transition‐metal‐free sp 2 –sp 3 cross‐couplings of electron‐rich aromatic systems can be used to convert 4 a and 5 a into the thienyl derivatives 16 (70 %) and 17 (84 %), respectively . Treatment of the primary boronic ester 4 a with bromobenzene under typical palladium‐catalyzed Suzuki cross‐coupling conditions affords 18 , a product that is not readily accessible through the transition‐metal‐free procedure employed for thienylation. Protodeboronation of the tertiary boronic ester 5 a affords 19 (90 %, 98:2 er) .…”

Section: Figurementioning

confidence: 88%

Ligand‐Controlled Regiodivergent Enantioselective Rhodium‐Catalyzed Alkene Hydroboration

2019

View full text Add to dashboard Cite

Regiocontrol in the rhodium‐catalyzed boration of vinyl arenes is typically dominated by the presence of the conjugated aryl substituent. However, small differences in TADDOL‐derived chiral monophosphite ligands can override this effect and direct rhodium‐catalyzed hydroboration of β‐aryl and β‐heteroaryl methylidenes by pinacolborane to selectively produce either chiral primary or tertiary borated products. The regiodivergent behavior is coupled with enantiodivergent addition of the borane. The nature of the TADDOL backbone substituents and that of the phosphite moiety function synergistically to direct the sense and extent of regioselectivity and enantioinduction. Twenty substrates are shown to undergo each reaction mode with regioselectivity values reaching greater than 20:1 and enantiomer ratios reaching up to 98:2. A variety of subsequent transformations illustrate the potential utility of each product.

show abstract

Modular Synthesis of Enantioenriched 1,1,2-Triarylethanes by an Enantioselective Arylboration and Cross-Coupling Sequence

Cited by 138 publications

References 82 publications

Synergistic Pd/Cu Catalysis in Organic Synthesis

Synergistic Pd/Cu Catalysis in Organic Synthesis

Copper‐Catalyzed Borylacylation of Activated Alkenes with Acid Chlorides

Ligand‐Controlled Regiodivergent Enantioselective Rhodium‐Catalyzed Alkene Hydroboration

Contact Info

Product

Resources

About