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      Enantioconvergent Reductive C(sp)−C(sp 3) Cross‐Coupling to Access Chiral α‐Alkynyl Phosphonates Under Dual Nickel/Photoredox Catalysis

      Author(s): 1 , 1 , 1
      Publication date (Electronic):
      Journal: Angewandte Chemie International Edition
      Publisher: Wiley

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          Abstract

          Transition‐metal‐catalyzed asymmetric carbon−carbon bond formation to forge phosphonates with an α‐chiral carbon center through C(sp 3)−C(sp 3) and C(sp 2)−C(sp 3) couplings has been successful. However, the enantioselective C(sp)−C(sp 3) coupling has not yet been disclosed. Reported herein is an unprecedented enantioconvergent cross‐coupling of alkynyl bromides and α‐bromo phosphonates to deliver chiral α‐alkynyl phosphonates.

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          Dual catalysis. Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis.

          J. C. Tellis, D. N. Primer, G A Molander (2014)
          The routine application of C(sp3)-hybridized nucleophiles in cross-coupling reactions remains an unsolved challenge in organic chemistry. The sluggish transmetalation rates observed for the preferred organoboron reagents in such transformations are a consequence of the two-electron mechanism underlying the standard catalytic approach. We describe a mechanistically distinct single-electron transfer-based strategy for the activation of organoboron reagents toward transmetalation that exhibits complementary reactivity patterns. Application of an iridium photoredox catalyst in tandem with a nickel catalyst effects the cross-coupling of potassium alkoxyalkyl- and benzyltrifluoroborates with an array of aryl bromides under exceptionally mild conditions (visible light, ambient temperature, no strong base). The transformation has been extended to the asymmetric and stereoconvergent cross-coupling of a secondary benzyltrifluoroborate.
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            Palladium-Catalyzed Coupling Reactions of Aryl Chlorides

            Adam Littke, Gregory Fu (2002)
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              Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis.

              Zhiwei Zuo, HUAN CONG, Wei Li … (2016)
              An asymmetric decarboxylative Csp(3)-Csp(2) cross-coupling has been achieved via the synergistic merger of photoredox and nickel catalysis. This mild, operationally simple protocol transforms a wide variety of naturally abundant α-amino acids and readily available aryl halides into valuable chiral benzylic amines in high enantiomeric excess, thereby producing motifs found in pharmacologically active agents.
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                Author and article information

                Contributors
                Journal
                Title: Angewandte Chemie International Edition
                Abbreviated Title: Angew Chem Int Ed
                Publisher: Wiley
                ISSN (Print): 1433-7851
                ISSN (Electronic): 1521-3773
                Publication date Created: April 24 2023
                Publication date (Electronic): March 28 2023
                Publication date (Print): April 24 2023
                Volume: 62
                Issue: 18
                Affiliations
                [1 ] Shanghai Key Laboratory of Chemical Assessment and Sustainability School of Chemical Science and Engineering Tongji University 1239 Siping Road Shanghai 200092 P. R. China
                Article
                DOI: 10.1002/anie.202218299
                SO-VID: 7f00d619-c13b-4384-8c65-5a319575460c
                Copyright © © 2023
                License:

                http://onlinelibrary.wiley.com/termsAndConditions#vor

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