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Pioneers and Influencers in Organometallic Chemistry: Professor Yao-Zeng Huang and His Three “Treasure Chests”
Organometallics ( IF 2.8 ) Pub Date : 2020-06-22 , DOI: 10.1021/acs.organomet.0c00391 Liang Deng
Organometallics ( IF 2.8 ) Pub Date : 2020-06-22 , DOI: 10.1021/acs.organomet.0c00391 Liang Deng
The “Pioneers and Influencers” project at Organometallics aims to highlight the careers of organometallic chemists who have made great contributions to the discipline and may not have gained the recognition they deserve. This set of editorials allows me to recall the founding fathers of organometallic chemistry in China. Many of these chemists were born at the beginning of the 20th century and had been active in the science arena for decades until the latter half of the century. In their era, international academic communications for Chinese scientists were not frequent as they are nowadays. As a result, these chemists have remained less known to the global scientific community. In this editorial, I wish to introduce one of the founding fathers, the late Professor Yao-Zeng Huang at the Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (Figure 1). Figure 1. Photograph of Professor Yao-Zeng Huang, taken in 1979. The electronic version of the photo was provided by the SIOC archive. Professor Huang joined the SIOC as a professor in 1949 and worked there until his death in 2002. He was the founder of the Laboratory of Organometallic Chemistry in SIOC and was appointed as the honorary director when the laboratory was set up in 1989. Years later, this laboratory was promoted to a State Key Laboratory, where I am now working as a professor. From this connection, I have had the opportunity to learn anecdotes about Professor Yao-Zeng Huang from his former co-workers and students. Professor Yong Tang, the director of the SIOC, was a Ph.D. student of Professor Huang and always recalls his Ph.D. supervisor with affection and admiration. He mentioned Professor Huang’s three “treasure chests”, basic research, applied research, and cultivating talents, which constitute a rich harvest in Professor Huang’s career and are also highly commended by Professor Huang’s acquaintances.(1,2) Professor Huang’s interest in basic research principally focused on organometallic chemistry and organoelement chemistry. I began to know Professor Huang’s research work when my group started a project on the group-transfer reactions of iron-bonded phosphonium ylides several years ago.(3) As a rookie in the field, I did a literature survey on ylide chemistry and was shocked to learn that Professor Huang had authored more than 100 papers on the chemistry of organoelement compounds of group 15 and 16 elements since his first publication on the topic in 1965.(4) Influenced by the training he received as a synthetic organic chemist in his early career, Professor Huang was interested in organoelement compounds and also focused on their synthetic applications. The representative output includes (i) the development of AsBun3-catalyzed olefination of aldehydes with α-halogenated carbonyl compounds,(5) which is the first example of a catalytic Wittig-type reaction (Scheme 1a), (ii) a detailed study of the reactions of quaternary stibonium salts [SbR3R′]X with base and organolithium reagents,(6) which led to the establishment of different trialkylstibine-mediated C–C bond formation reactions (Scheme 1b), and (iii) the development of diisobutyltellurium-catalyzed cyclopropanation reactions of allylic bromide with α,β-unsaturated ketones,(7) which is the first example of a catalytic ylide cyclopropanation reaction (Scheme 1c). Summaries of his studies on arsonium ylides,(8) organoantimony compounds,(9) and organotelluronium compounds(10) can be found in his three review papers in Advances in Organometallic Chemistry, Accounts of Chemical Research, and Tetrahedron, respectively. The 1950s had witnessed a fast development of organometallic chemistry, as reflected by the discovery of ferrocene, the Wittig reaction, and hydroboration reactions. Stimulated by these findings, Professor Huang acutely foresaw the wide vista of organoelement compounds and organo-transition-metal compounds in organic synthesis(11) and initiated his research on organoarsine and organochromium compounds in the early 1960s. The two projects then flourished in the 1980s. The former grew into a broader topic of organoelement compounds of the group 15 and 16 elements as mentioned above. The latter led to the seminal findings on transition-metal-catalyzed reactions of perfluorinated organic compounds. Coincidentally, the metal catalysts that Professor Huang preferred are zerovalent transition-metal complexes, and they are also among my favorites. Along with his co-workers, Professor Huang investigated the interaction of bis(benzene)chromium(0) with perfluorinated alkenes and alkynes and disclosed the ability of the chromium complex in catalyzing the oligmerization of hexafluoropropene(12) and the polymerization of hexafluorobut-2-yne(13) and perfluoro-2-alkynenitriles(14) (Scheme 2a,b). These chromium-catalyzed reactions of perfluorinated organic compounds are in contrast to many of the contemporary studies that employed late transition metals and operated in a stoichiometric manner.(15) In the exploration of zerovalent group 10 metal complexes, Professor Huang and his Ph.D. student Qi-Lin Zhou, who is now a professor at Nankai University, were able to develop M(PPh3)4 (M = Ni, Pd, Pt)-catalyzed coupling reactions of perfluoroalkyl iodides with tertiary amines(16,17) and arenes(18,19) in the 1980s, by which perfluoroalkyl-substituted enamines and arenes can be generated (Scheme 2c,d). Notably, the nickel-catalyzed fluoroalkylation reactions of arenes are the first examples of this type employing metal catalysts,(18) and they still inspire the recent development of metal-catalyzed perfluoroalkylation reactions.(20) Like his interests in basic research, Professor Huang’s dedication to applied research and education had also led to great achievements. By reading his biography,(1,2,21) I got to know that, in the 1950s and 1960s, Professor Huang had led the research teams in SIOC on several application-oriented projects, such as the extraction of chlortetracycline, the preparation of high-quality polytetrafluoroethylene, the preparation of fluorinated lubricants for the separation of uranium isotopes, and the preparation of sodium perfluoroalkyl sulfates for fire-extinguishing agents. The technology developed by these projects was successfully implemented in pharmaceutical companies and factories. In the late 1970s, Professor Huang guided a research project on electrochemical metalizing solutions. Some of the products achieved nationwide commercialization in the 1980s. Professor Huang was recognized as a great mentor (Figure 2). Among the representatives of the talents in his “treasure chest” are his 17 Ph.D.s. Though the quantity is not large, all of them are very successful in their careers as entrepreneurs, research scientists, and professors. In fact, three of them are now Members of Chinese Academy of Sciences. Figure 2. Professor Yao-Zeng Huang, his wife Ms. Qi-Dian You, and his students. Front row, left to right: Wei-Bo Wang, Professor Yao-Zeng Huang, Ms. Qi-Dian You, Chen Chen, Shao-Wei Li. Back row, left to right: Wei-Min Qiu, Jian-Qiang Zhou, Gui-Sheng Li, Zuowei Xie, Jian-Hua Yang, Yu-Jin Huang, Shou-Yuan Lin, Yi Liao, Qi-Lin Zhou. The photograph was taken in his apartment in 1987. The electronic version of the photo was provided by the SIOC archive. In addition to his three “Treasure Chests”, Professor Huang was also well-known for his hobby of classical Chinese poetry. He grew up in a literary family and was skilled in writing these types of poems. Shown here are two short descriptions from his autobiography.(21) In celebrating the third China–Japan–USA Trilateral Seminar on Organometallic Chemistry held at Santa Cruz in 1984, Professor Huang wrote “Enchanting scenery enlivens our events. Triplet meeting consolidates the peaceful “Pac”. Organometallics catalyze various things. Eternal friendship joins hearts with hearts.” (In Chinese: 
, 
. 
, 
.) At the age of 80, he wrote a poem to express his gratitude to his supervisor, the late Professor Chang-Kong Chuang, who was the founding director of the SIOC: Late professor Chuang led me into scientific study. His salutary influence of education stays alive in my memory: A known proverb you should remembere forever, “Initiative leads one to success and imitation leads one to failure.” (In Chinese: 
, 
, “
, 
”.) From the poems, one feels Professor Huang’s rich affection, modesty, and deep love of chemistry. As a brief biography, Professor Yao-Zeng Huang was born in Jiangsu Province, China, in 1912. He had his bachelor’s degree from the Department of Chemistry, National Central University in Nanjing in 1934. He worked at the Institute of Chemistry, Academia Sinica, in Shanghai as a research assistant and an associate research fellow before 1949, and then at the SIOC as associate professor and research professor. He had served as the founding Editor-in-Chief of Chinese Organic Chemistry, as a member of the advisory board of Heteroatom Chemistry, as the cochairman of the China–Japan–USA Trilateral Seminar on Organometallic Chemistry, as a deputy director of the SIOC, and as a member of the Standing Committee of the Chinese Chemical Society. He was a Member of the Chinese Academy of Sciences, the awardee of three National Natural Sciences Awards (1982, 1993, and 2001), the winner of the World Academy of Sciences Award in Basic Sciences (1994), and a laureate of the HOLEUNG HO LEE Achievement Prize in Chemistry (1997). In memory of his contribution to the scientific community, the Chinese Chemical Society established a distinguished award after his name, the Huang Yao-Zeng Organometallic Chemistry Award, in 2003.(22) Professor Huang’s impactful work in basic and applied research and his long-term service to the science community have well illustrated his role as a pioneer and influencer in organometallic chemistry and organoelement chemistry. Views expressed in this editorial are those of the author and not necessarily the views of the ACS. A special thanks goes to Prof. Yong Tang, Prof. Zuowei Xie, and Prof. Qi-Lin Zhou for insightful discussions and Ms. Zhijing Huang at the SIOC archive for the images presented in this editorial. This article references 22 other publications.
更新日期：2020-07-13
, . , .) At the age of 80, he wrote a poem to express his gratitude to his supervisor, the late Professor Chang-Kong Chuang, who was the founding director of the SIOC: Late professor Chuang led me into scientific study. His salutary influence of education stays alive in my memory: A known proverb you should remembere forever, “Initiative leads one to success and imitation leads one to failure.” (In Chinese: , , “, ”.) From the poems, one feels Professor Huang’s rich affection, modesty, and deep love of chemistry. As a brief biography, Professor Yao-Zeng Huang was born in Jiangsu Province, China, in 1912. He had his bachelor’s degree from the Department of Chemistry, National Central University in Nanjing in 1934. He worked at the Institute of Chemistry, Academia Sinica, in Shanghai as a research assistant and an associate research fellow before 1949, and then at the SIOC as associate professor and research professor. He had served as the founding Editor-in-Chief of Chinese Organic Chemistry, as a member of the advisory board of Heteroatom Chemistry, as the cochairman of the China–Japan–USA Trilateral Seminar on Organometallic Chemistry, as a deputy director of the SIOC, and as a member of the Standing Committee of the Chinese Chemical Society. He was a Member of the Chinese Academy of Sciences, the awardee of three National Natural Sciences Awards (1982, 1993, and 2001), the winner of the World Academy of Sciences Award in Basic Sciences (1994), and a laureate of the HOLEUNG HO LEE Achievement Prize in Chemistry (1997). In memory of his contribution to the scientific community, the Chinese Chemical Society established a distinguished award after his name, the Huang Yao-Zeng Organometallic Chemistry Award, in 2003.(22) Professor Huang’s impactful work in basic and applied research and his long-term service to the science community have well illustrated his role as a pioneer and influencer in organometallic chemistry and organoelement chemistry. Views expressed in this editorial are those of the author and not necessarily the views of the ACS. A special thanks goes to Prof. Yong Tang, Prof. Zuowei Xie, and Prof. Qi-Lin Zhou for insightful discussions and Ms. Zhijing Huang at the SIOC archive for the images presented in this editorial. This article references 22 other publications.
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