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Abstract Simple access to aryl sulfinates from aryl iodides and bromides is reported using an inexpensive Ni‐electrocatalytic protocol. The reaction exhibits a broad scope, uses stock solution of simple SO2as sulfur source, and can be scaled up in batch and recycle flow settings. The limitations of this reaction are clearly shown and put into context by benchmarking with state‐of‐the‐art Pd‐based methods.
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Chemoselective, Scalable Nickel‐Electrocatalytic O ‐Arylation of Alcohols
Abstract The formation of aryl‐alkyl ether bonds through cross coupling of alcohols with aryl halides represents a useful strategic departure from classical SN2 methods. Numerous tactics relying on Pd‐, Cu‐, and Ni‐based catalytic systems have emerged over the past several years. Herein we disclose a Ni‐catalyzed electrochemically driven protocol to achieve this useful transformation with a broad substrate scope in an operationally simple way. This electrochemical method does not require strong base, exogenous expensive transition metal catalysts (e.g., Ir, Ru), and can easily be scaled up in either a batch or flow setting. Interestingly, e‐etherification exhibits an enhanced substrate scope over the mechanistically related photochemical variant as it tolerates tertiary amine functional groups in the alcohol nucleophile.
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- Award ID(s):
- 2002158
- PAR ID:
- 10287310
- Publisher / Repository:
- Wiley Blackwell (John Wiley & Sons)
- Date Published:
- Journal Name:
- Angewandte Chemie International Edition
- Volume:
- 60
- Issue:
- 38
- ISSN:
- 1433-7851
- Page Range / eLocation ID:
- p. 20700-20705
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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