4.8 Article

Divergent Dehydrogenative Coupling of Indolines with Alcohols

Journal

ACS CATALYSIS
Volume 7, Issue 3, Pages 1831-1835

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b03667

Keywords

dehydrogenation; indole; alcohol; iridium; cross coupling

Funding

  1. National Natural Science Foundation of China [21473109]
  2. Science and Technology Program of Shaanxi Province [2016KJXX-26]
  3. Program for Changjiang Scholars and Innovative Research Team in University [IRT_14R33]
  4. 111 Project [B14041]
  5. Engineering and Physical Sciences Research Council [EP/K039687/1] Funding Source: researchfish
  6. EPSRC [EP/K039687/1] Funding Source: UKRI

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The dehydrogenative coupling of indolines with alcohols catalyzed by an iridium complex has been achieved to afford both N- and C3-alkylated indoles selectively, by simply changing the addition time of a base additive. The iridacycle catalyst plays multiple roles in these reactions, which dehydrogenates both amines and alcohols and catalyzes the coupling reactions. Mechanistic studies reveal that a borrowing hydrogen-dehydrogenation process and a dehydrogenation-borrowing hydrogen process are involved in N-alkylation and C3-alkylation reactions, respectively. The C3-alkylation reaction involves the direct coupling of two sp3 carbon centers.

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