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Derivatization of 2...
Derivatization of 2,1,3-Benzothiadiazole via Regioselective C–H Functionalization and Aryne Reactivity
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- Kunz, Susanna (författare)
- Uppsala universitet,Institutionen för kemi - BMC
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- Barnå, Fredrik (författare)
- Uppsala universitet,Organisk kemi
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- Posada Urrutia, Mauricio (författare)
- Uppsala universitet,Organisk kemi,Christine Dyrager
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- Ingner, Fredric J. L. (författare)
- Uppsala universitet,Organisk kemi
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- Martínez-Topete, Andrea (författare)
- Uppsala universitet,Institutionen för kemi - BMC
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- Orthaber, Andreas, 1979- (författare)
- Uppsala universitet,Syntetisk molekylär kemi
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- Gates, Paul J. (författare)
- School of Chemistry, University of Bristol, Cantock’s Close, Clifton, Bristol BS8 1TS, U.K.
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- Pilarski, Lukasz T., 1981- (författare)
- Uppsala universitet,Organisk kemi
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- Dyrager, Christine (författare)
- Uppsala universitet,Organisk kemi
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(creator_code:org_t)
- American Chemical Society (ACS), 2024
- 2024
- Engelska.
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Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 89:9, s. 6138-6148
- Relaterad länk:
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https://doi.org/10.1...
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https://uu.diva-port... (primary) (Raw object)
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
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- Despite growing interest in 2,1,3-benzothiadiazole (BTD) as an integral component of many functional molecules, methods for the functionalization of its benzenoid ring have remained limited, and many even simply decorated BTDs have required de novo synthesis. We show that regioselective Ir-catalyzed C–H borylation allows access to versatile 5-boryl or 4,6-diboryl BTD building blocks, which undergo functionalization at the C4, C5, C6, and C7 positions. The optimization and regioselectivity of C–H borylation are discussed. A broad reaction scope is presented, encompassing ipso substitution at the C–B bond, the first examples of ortho-directed C–H functionalization of BTD, ring closing reactions to generate fused ring systems, as well as the generation and capture reactions of novel BTD-based heteroarynes. The regioselectivity of the latter is discussed with reference to the Aryne Distortion Model.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
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