I'm referring to FAA Part 91 and 135 operations (or similar, EASA) and the maximum duration of one single flight (not the maximum duty time per day / week / month). If any, what are the legal flight time limitations for single pilots? In other words, which flight time requires more than one pilot?
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Short answer: no limit for private Part 91 operations, otherwise 8 hours.
The only Part 91 regulations I can see on this are in Subpart K - Fractional Ownership Operations. There's too much information to quote here, but see 91.1057, 1059, 1061 and 1062. For a single-pilot operation the basic limit is 8 hours, per 1059(b):
(b) Except as provided in paragraph (c) of this section, during any 24 consecutive hours the total flight time of the assigned flight, when added to any commercial flying by that flight crewmember, may not exceed—
(1) 8 hours for a flight crew consisting of one pilot;
There's no restriction for typical private GA pilots, apart from 91.13 on careless or reckless operation. Flying while very tired could easily be seen as reckless if it affects the safety of a flight.
As for Part 135, the regulations are in Subpart F—Crewmember Flight Time and Duty Period Limitations and Rest Requirements. Again, there's too much to quote but the basic limit for a single pilot is 8 hours, per 135.267(b):
(b) Except as provided in paragraph (c) of this section, during any 24 consecutive hours the total flight time of the assigned flight when added to any other commercial flying by that flight crewmember may not exceed—
(1) 8 hours for a flight crew consisting of one pilot;
Your second question about when an additional pilot is required is a bit unclear. A second pilot is usually required because of the type of aircraft or operation, not the length of a flight. But I know very little about Part 135 so I may be wrong; in any case, I think it would probably be better as a separate question.
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$\begingroup$ In reference to your last paragraph, if there is more than 8 hours of flying in a day, there is the option to add a second, third, and even fourth pilot in order to take advantage of the extended flight time available to those crews. This, of course, assumes that you have other qualified crewmembers and appropriate rest facilities for the "off-duty" crewmembers. $\endgroup$ Commented Feb 8, 2018 at 19:25