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Cobalt(III) Porphyrin-Decorated Stereoregular Polyisocyanides Enable Highly Effective Cooperative Catalysis for Hydration of Alkynes
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-10-29 , DOI: 10.1021/acscatal.1c04062 Shu-Ming Kang 1 , Shan-Shan Han 1 , Yuan-Yuan Zhu 1 , Zong-Quan Wu 1
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-10-29 , DOI: 10.1021/acscatal.1c04062 Shu-Ming Kang 1 , Shan-Shan Han 1 , Yuan-Yuan Zhu 1 , Zong-Quan Wu 1
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We report a facile strategy to boost cooperative catalysis for alkyne hydration using polymer-supported catalysts. In this work, cobalt(III) porphyrin is deliberately decorated onto stereoregular polyisocyanides to synthesize the functional polymer P1-Co. Owing to the preorganization of the rigid polymer skeleton, adjacent pendant cobalt(III) porphyrins are arranged in parallel with an average distance of ∼0.9 nm, in which both the nucleophilic and electrophilic substrates can be dual-activated. The catalytic effectivity is investigated via catalytic hydration of a series of terminal and internal alkynes. P1-Co exhibits high activity to afford the desired products in good to excellent conversions at low catalyst loadings (0.1 mol % for terminal alkynes and 0.3 mol % for internal alkynes). Conversely, the irregular polymeric analogs P2-Co and P3-Co as well as the small-molecule control C1-Co perform poorly due to the lack of a cooperative catalysis approach. To demonstrate its potential application in the pharmaceutical industry, the formal syntheses of four drugs involving hydration of alkynes as the key step are achieved in excellent yields.
中文翻译：
钴 (III) 卟啉修饰的立体规则聚异氰化物能够高效协同催化炔烃的水合
我们报告了一种使用聚合物负载催化剂促进炔烃水合协同催化的简便策略。在这项工作中，钴 (III) 卟啉被故意装饰到有规立构的聚异氰化物上以合成功能性聚合物P1-Co。由于刚性聚合物骨架的预组织，相邻的侧链钴（III）卟啉以~0.9 nm的平均距离平行排列，其中亲核和亲电底物都可以被双重激活。通过一系列末端和内部炔烃的催化水合研究催化效率。P1-钴表现出高活性以在低催化剂负载（末端炔烃为 0.1 mol% 和内部炔烃为 0.3 mol%）下以良好到出色的转化率提供所需的产物。相反，由于缺乏协同催化方法，不规则聚合物类似物P2-Co和P3-Co以及小分子对照C1-Co表现不佳。为了证明其在制药行业的潜在应用，以炔烃的水合为关键步骤的四种药物的正式合成以优异的收率实现。
更新日期：2021-11-19
中文翻译：
钴 (III) 卟啉修饰的立体规则聚异氰化物能够高效协同催化炔烃的水合
我们报告了一种使用聚合物负载催化剂促进炔烃水合协同催化的简便策略。在这项工作中，钴 (III) 卟啉被故意装饰到有规立构的聚异氰化物上以合成功能性聚合物P1-Co。由于刚性聚合物骨架的预组织，相邻的侧链钴（III）卟啉以~0.9 nm的平均距离平行排列，其中亲核和亲电底物都可以被双重激活。通过一系列末端和内部炔烃的催化水合研究催化效率。P1-钴表现出高活性以在低催化剂负载（末端炔烃为 0.1 mol% 和内部炔烃为 0.3 mol%）下以良好到出色的转化率提供所需的产物。相反，由于缺乏协同催化方法，不规则聚合物类似物P2-Co和P3-Co以及小分子对照C1-Co表现不佳。为了证明其在制药行业的潜在应用，以炔烃的水合为关键步骤的四种药物的正式合成以优异的收率实现。
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