America Online on Tuesday sealed a $1 billion transaction to sell a 5 percent stake to Google Inc. in a deal that deepens the ties binding two of the Web's most popular Web sites while thwarting Microsoft Corp.'s efforts to grab a larger piece of the booming Internet advertising market.
Approving the expanded alliance had been considered a mere formality last Friday when AOL's corporate parent, Time Warner Inc., abruptly ended several months of negotiations with Microsoft, which had hoped to supplant Google as AOL's main advertising partner.
Many of the details, including a plan that may display more graphical ads on some of Google's traditionally sparse Web pages, had been leaked to the media in the last few days.
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